JP4078695B2 - Method for producing aromatic ether - Google Patents
Method for producing aromatic ether Download PDFInfo
- Publication number
- JP4078695B2 JP4078695B2 JP32319697A JP32319697A JP4078695B2 JP 4078695 B2 JP4078695 B2 JP 4078695B2 JP 32319697 A JP32319697 A JP 32319697A JP 32319697 A JP32319697 A JP 32319697A JP 4078695 B2 JP4078695 B2 JP 4078695B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- substituted
- group
- tertiarybutoxy
- sodium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000008378 aryl ethers Chemical class 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 150000002941 palladium compounds Chemical class 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
- 229910052717 sulfur Chemical group 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229910052731 fluorine Chemical group 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- 239000011630 iodine Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- -1 alkoxy copper compound Chemical class 0.000 description 59
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 9
- 150000001502 aryl halides Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 150000004820 halides Chemical group 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YFNONBGXNFCTMM-YMHOBSDZSA-N butoxybenzene Chemical group CCCCO[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 YFNONBGXNFCTMM-YMHOBSDZSA-N 0.000 description 3
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- SCZXFZRJDVZMJI-UHFFFAOYSA-N 1-bromo-2,4,5-trimethylbenzene Chemical compound CC1=CC(C)=C(Br)C=C1C SCZXFZRJDVZMJI-UHFFFAOYSA-N 0.000 description 2
- RINOYHWVBUKAQE-UHFFFAOYSA-N 1-iodo-2-methylbenzene Chemical compound CC1=CC=CC=C1I RINOYHWVBUKAQE-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- ZPRQXVPYQGBZON-UHFFFAOYSA-N 2-bromo-1h-indole Chemical compound C1=CC=C2NC(Br)=CC2=C1 ZPRQXVPYQGBZON-UHFFFAOYSA-N 0.000 description 2
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- SMFFZOQLHYIRDA-UHFFFAOYSA-N 3,4-dimethoxyphenol Chemical compound COC1=CC=C(O)C=C1OC SMFFZOQLHYIRDA-UHFFFAOYSA-N 0.000 description 2
- MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 2
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- LTRVAZKHJRYLRJ-UHFFFAOYSA-N lithium;butan-1-olate Chemical group [Li+].CCCC[O-] LTRVAZKHJRYLRJ-UHFFFAOYSA-N 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- ZBNNKSSSCSTNNK-UHFFFAOYSA-M sodium;naphthalen-1-olate Chemical compound [Na+].C1=CC=C2C([O-])=CC=CC2=C1 ZBNNKSSSCSTNNK-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GQHWSLKNULCZGI-UHFFFAOYSA-N trifluoromethoxybenzene Chemical compound FC(F)(F)OC1=CC=CC=C1 GQHWSLKNULCZGI-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- AUAZNDJHTMXNSN-UHFFFAOYSA-N (2-bromophenoxy)-tert-butyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OC1=CC=CC=C1Br AUAZNDJHTMXNSN-UHFFFAOYSA-N 0.000 description 1
- MODQBMCQXFQKDR-UHFFFAOYSA-N (2-bromopyrrol-1-yl)-trimethylsilane Chemical compound C[Si](C)(C)N1C=CC=C1Br MODQBMCQXFQKDR-UHFFFAOYSA-N 0.000 description 1
- BFRHMVJJJGUHDI-UHFFFAOYSA-N (3-bromophenoxy)-tert-butyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OC1=CC=CC(Br)=C1 BFRHMVJJJGUHDI-UHFFFAOYSA-N 0.000 description 1
- DLGZGLKSNRKLSM-UHFFFAOYSA-N (4-bromophenoxy)-tert-butyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OC1=CC=C(Br)C=C1 DLGZGLKSNRKLSM-UHFFFAOYSA-N 0.000 description 1
- ITVUPWDTDWMACZ-UHFFFAOYSA-N (4-phenoxyphenyl)-phenylmethanone Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 ITVUPWDTDWMACZ-UHFFFAOYSA-N 0.000 description 1
- SYSZENVIJHPFNL-UHFFFAOYSA-N (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform B (protein) Chemical compound COC1=CC=C(I)C=C1 SYSZENVIJHPFNL-UHFFFAOYSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- SDUILFAEUHNOAS-UHFFFAOYSA-N 1,2-bis[(2-methylpropan-2-yl)oxy]benzene Chemical compound CC(C)(C)OC1=CC=CC=C1OC(C)(C)C SDUILFAEUHNOAS-UHFFFAOYSA-N 0.000 description 1
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 1
- SLLDDDJWIRFAGU-UHFFFAOYSA-N 1,2-dichlorocycloocta-1,5-diene Chemical compound ClC1=C(Cl)CCC=CCC1 SLLDDDJWIRFAGU-UHFFFAOYSA-N 0.000 description 1
- KYWFNEYPIIIMNM-UHFFFAOYSA-N 1,2-dimethoxy-4-[(2-methylpropan-2-yl)oxy]benzene Chemical compound COC1=CC=C(OC(C)(C)C)C=C1OC KYWFNEYPIIIMNM-UHFFFAOYSA-N 0.000 description 1
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 description 1
- XKEFYDZQGKAQCN-UHFFFAOYSA-N 1,3,5-trichlorobenzene Chemical compound ClC1=CC(Cl)=CC(Cl)=C1 XKEFYDZQGKAQCN-UHFFFAOYSA-N 0.000 description 1
- WXLJJIHGDBUBJM-UHFFFAOYSA-N 1,3,5-triiodobenzene Chemical compound IC1=CC(I)=CC(I)=C1 WXLJJIHGDBUBJM-UHFFFAOYSA-N 0.000 description 1
- HJQRITCAXSBOPC-UHFFFAOYSA-N 1,3,5-tris(4-bromophenyl)benzene Chemical compound C1=CC(Br)=CC=C1C1=CC(C=2C=CC(Br)=CC=2)=CC(C=2C=CC(Br)=CC=2)=C1 HJQRITCAXSBOPC-UHFFFAOYSA-N 0.000 description 1
- MMOYVYSPNDJNOT-UHFFFAOYSA-N 1,3,5-tris[(2-methylpropan-2-yl)oxy]benzene Chemical compound CC(C)(C)OC1=CC(OC(C)(C)C)=CC(OC(C)(C)C)=C1 MMOYVYSPNDJNOT-UHFFFAOYSA-N 0.000 description 1
- NFOCLLJDPTWUKX-UHFFFAOYSA-N 1,3-benzodioxol-5-yloxy(trimethyl)silane Chemical compound C[Si](C)(C)OC1=CC=C2OCOC2=C1 NFOCLLJDPTWUKX-UHFFFAOYSA-N 0.000 description 1
- HIQUVLYPUNAUEL-UHFFFAOYSA-N 1,3-bis[(2-methylpropan-2-yl)oxy]benzene Chemical compound CC(C)(C)OC1=CC=CC(OC(C)(C)C)=C1 HIQUVLYPUNAUEL-UHFFFAOYSA-N 0.000 description 1
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 1
- UPZHSZZEPVMYON-UHFFFAOYSA-N 1,3-dichloro-5-[(2-methylpropan-2-yl)oxy]benzene Chemical compound CC(C)(C)OC1=CC(Cl)=CC(Cl)=C1 UPZHSZZEPVMYON-UHFFFAOYSA-N 0.000 description 1
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FMDDSXFJMWQYTJ-UHFFFAOYSA-N 1,4-bis[(2-methylpropan-2-yl)oxy]benzene Chemical compound CC(C)(C)OC1=CC=C(OC(C)(C)C)C=C1 FMDDSXFJMWQYTJ-UHFFFAOYSA-N 0.000 description 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
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- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
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- 239000007983 Tris buffer Substances 0.000 description 1
- NOZSKQYGIIOONC-UHFFFAOYSA-N [4-[(2-methylpropan-2-yl)oxy]phenyl]-phenylmethanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)C1=CC=CC=C1 NOZSKQYGIIOONC-UHFFFAOYSA-N 0.000 description 1
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- RBYGDVHOECIAFC-UHFFFAOYSA-L acetonitrile;palladium(2+);dichloride Chemical compound [Cl-].[Cl-].[Pd+2].CC#N.CC#N RBYGDVHOECIAFC-UHFFFAOYSA-L 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- VLLNJDMHDJRNFK-UHFFFAOYSA-N adamantan-1-ol Chemical compound C1C(C2)CC3CC2CC1(O)C3 VLLNJDMHDJRNFK-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000001499 aryl bromides Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- WXNOJTUTEXAZLD-UHFFFAOYSA-L benzonitrile;dichloropalladium Chemical compound Cl[Pd]Cl.N#CC1=CC=CC=C1.N#CC1=CC=CC=C1 WXNOJTUTEXAZLD-UHFFFAOYSA-L 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical group CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NXTYDKDYJFSZSO-UHFFFAOYSA-N butyl-hydroxy-dimethylsilane Chemical group CCCC[Si](C)(C)O NXTYDKDYJFSZSO-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- LNAMMBFJMYMQTO-FNEBRGMMSA-N chloroform;(1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].ClC(Cl)Cl.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 LNAMMBFJMYMQTO-FNEBRGMMSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- UNZAHHRCRMZNFJ-UHFFFAOYSA-N cyclopenta-1,3-diene 1-(2-iodocyclopenta-2,4-dien-1-yl)-N,N-dimethylmethanamine iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.CN(C)C[c-]1cccc1I UNZAHHRCRMZNFJ-UHFFFAOYSA-N 0.000 description 1
- JMMPIVZDWBCEFB-UHFFFAOYSA-N cyclopenta-1,3-diene 5-iodocyclopenta-1,3-diene iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.Ic1cc[cH-]c1 JMMPIVZDWBCEFB-UHFFFAOYSA-N 0.000 description 1
- LOPINJUVMVOQSS-UHFFFAOYSA-N cyclopenta-2,4-dien-1-yl(phenyl)phosphane;iron(2+) Chemical compound [Fe+2].C1=CC=C[C-]1PC1=CC=CC=C1.C1=CC=C[C-]1PC1=CC=CC=C1 LOPINJUVMVOQSS-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- QIEAOJHJHCCINB-UHFFFAOYSA-M lithium 2-(dimethylamino)phenolate Chemical compound CN(C1=C(C=CC=C1)[O-])C.[Li+] QIEAOJHJHCCINB-UHFFFAOYSA-M 0.000 description 1
- JPNHSJZYNRIQSQ-UHFFFAOYSA-M lithium 2-bromophenolate Chemical compound BrC1=C(C=CC=C1)[O-].[Li+] JPNHSJZYNRIQSQ-UHFFFAOYSA-M 0.000 description 1
- FEODYFRNIVOJMD-UHFFFAOYSA-M lithium 2-formylphenolate Chemical compound [Li+].[O-]c1ccccc1C=O FEODYFRNIVOJMD-UHFFFAOYSA-M 0.000 description 1
- DPZKYOBXEQZXHW-UHFFFAOYSA-M lithium 4-bromophenolate Chemical compound BrC1=CC=C(O[Li])C=C1 DPZKYOBXEQZXHW-UHFFFAOYSA-M 0.000 description 1
- RGZKHWXRHNRCJY-UHFFFAOYSA-M lithium 4-chlorophenolate Chemical compound [Li+].[O-]C1=CC=C(Cl)C=C1 RGZKHWXRHNRCJY-UHFFFAOYSA-M 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
- TYHOGVXXAWLQLY-UHFFFAOYSA-M lithium naphthalen-2-olate Chemical compound [Li+].C1=CC=CC2=CC([O-])=CC=C21 TYHOGVXXAWLQLY-UHFFFAOYSA-M 0.000 description 1
- HDKVJPLOHJJUJB-UHFFFAOYSA-N lithium triphenylmethanolate Chemical group C1(=CC=CC=C1)C([O-])(C1=CC=CC=C1)C1=CC=CC=C1.[Li+] HDKVJPLOHJJUJB-UHFFFAOYSA-N 0.000 description 1
- XEIPYWXDVTVONX-UHFFFAOYSA-N lithium;(4-methoxyphenyl)methanolate Chemical compound [Li+].COC1=CC=C(C[O-])C=C1 XEIPYWXDVTVONX-UHFFFAOYSA-N 0.000 description 1
- WXFJHGBPLFDLAC-UHFFFAOYSA-M lithium;2-methylphenolate Chemical compound [Li+].CC1=CC=CC=C1[O-] WXFJHGBPLFDLAC-UHFFFAOYSA-M 0.000 description 1
- PAACONZJUGFCHT-UHFFFAOYSA-M lithium;3-(dimethylamino)phenolate Chemical compound [Li+].CN(C)C1=CC=CC([O-])=C1 PAACONZJUGFCHT-UHFFFAOYSA-M 0.000 description 1
- XVTPFPXYRPTKIH-UHFFFAOYSA-M lithium;3-methylphenolate Chemical compound [Li+].CC1=CC=CC([O-])=C1 XVTPFPXYRPTKIH-UHFFFAOYSA-M 0.000 description 1
- OONWLILMXMWOMG-UHFFFAOYSA-M lithium;4-methylphenolate Chemical compound [Li+].CC1=CC=C([O-])C=C1 OONWLILMXMWOMG-UHFFFAOYSA-M 0.000 description 1
- ZBPRKOADIHMLIH-UHFFFAOYSA-N lithium;adamantan-1-olate Chemical group [Li+].C1C(C2)CC3CC2CC1([O-])C3 ZBPRKOADIHMLIH-UHFFFAOYSA-N 0.000 description 1
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
- XAVQZBGEXVFCJI-UHFFFAOYSA-M lithium;phenoxide Chemical compound [Li+].[O-]C1=CC=CC=C1 XAVQZBGEXVFCJI-UHFFFAOYSA-M 0.000 description 1
- HQWALQRCKGBWOV-UHFFFAOYSA-N lithium;triethyl(oxido)silane Chemical compound [Li+].CC[Si]([O-])(CC)CC HQWALQRCKGBWOV-UHFFFAOYSA-N 0.000 description 1
- OXOZHAWWRPCVGL-UHFFFAOYSA-N lithium;trimethyl(oxido)silane Chemical compound [Li+].C[Si](C)(C)[O-] OXOZHAWWRPCVGL-UHFFFAOYSA-N 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- RHXJDGNEUKBRKB-UHFFFAOYSA-N n,n-dimethyl-3-[(2-methylpropan-2-yl)oxy]aniline Chemical compound CN(C)C1=CC=CC(OC(C)(C)C)=C1 RHXJDGNEUKBRKB-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- PBDBXAQKXCXZCJ-UHFFFAOYSA-L palladium(2+);2,2,2-trifluoroacetate Chemical compound [Pd+2].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F PBDBXAQKXCXZCJ-UHFFFAOYSA-L 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 1
- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 description 1
- QULYNCCPRWKEMF-UHFFFAOYSA-N parachlorobenzotrifluoride Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1 QULYNCCPRWKEMF-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- IVCXGIGJTKJQFO-UHFFFAOYSA-M potassium;2-bromophenolate Chemical compound [K+].[O-]C1=CC=CC=C1Br IVCXGIGJTKJQFO-UHFFFAOYSA-M 0.000 description 1
- KSLKDKJNBJAMEG-UHFFFAOYSA-M potassium;2-chlorophenolate Chemical compound [K+].[O-]C1=CC=CC=C1Cl KSLKDKJNBJAMEG-UHFFFAOYSA-M 0.000 description 1
- BMBFVMNEJBZJTG-UHFFFAOYSA-M potassium;2-formylphenolate Chemical compound [K+].[O-]C1=CC=CC=C1C=O BMBFVMNEJBZJTG-UHFFFAOYSA-M 0.000 description 1
- ONUTZSPPHDDIOF-UHFFFAOYSA-M potassium;2-methylphenolate Chemical compound [K+].CC1=CC=CC=C1[O-] ONUTZSPPHDDIOF-UHFFFAOYSA-M 0.000 description 1
- NGLNLVCCWLLRBM-UHFFFAOYSA-M potassium;3,4-dimethylphenolate Chemical compound [K+].CC1=CC=C([O-])C=C1C NGLNLVCCWLLRBM-UHFFFAOYSA-M 0.000 description 1
- KPHPQOKTMUVNGR-UHFFFAOYSA-M potassium;3-(dimethylamino)phenolate Chemical compound [K+].CN(C)C1=CC=CC([O-])=C1 KPHPQOKTMUVNGR-UHFFFAOYSA-M 0.000 description 1
- OXHWDHKOQRPTTE-UHFFFAOYSA-M potassium;4-bromophenolate Chemical compound [K+].[O-]C1=CC=C(Br)C=C1 OXHWDHKOQRPTTE-UHFFFAOYSA-M 0.000 description 1
- HMSLXWQWEJXFFR-UHFFFAOYSA-M potassium;4-chlorophenolate Chemical compound [K+].[O-]C1=CC=C(Cl)C=C1 HMSLXWQWEJXFFR-UHFFFAOYSA-M 0.000 description 1
- YBMLSFPMJMAFOD-UHFFFAOYSA-M potassium;4-formylphenolate Chemical compound [K+].[O-]C1=CC=C(C=O)C=C1 YBMLSFPMJMAFOD-UHFFFAOYSA-M 0.000 description 1
- RRAHCFJFWDVGGZ-UHFFFAOYSA-M potassium;4-methylphenolate Chemical compound [K+].CC1=CC=C([O-])C=C1 RRAHCFJFWDVGGZ-UHFFFAOYSA-M 0.000 description 1
- AKCXVUZCFGJVCX-UHFFFAOYSA-M potassium;naphthalen-1-olate Chemical compound [K+].C1=CC=C2C([O-])=CC=CC2=C1 AKCXVUZCFGJVCX-UHFFFAOYSA-M 0.000 description 1
- NIXTUUCERQXALH-UHFFFAOYSA-M potassium;naphthalen-2-olate Chemical compound [K+].C1=CC=CC2=CC([O-])=CC=C21 NIXTUUCERQXALH-UHFFFAOYSA-M 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- BRZFUJPZZUJAKR-UHFFFAOYSA-N potassium;phenylmethanolate Chemical group [K+].[O-]CC1=CC=CC=C1 BRZFUJPZZUJAKR-UHFFFAOYSA-N 0.000 description 1
- YTJYCWNMRAYWLV-UHFFFAOYSA-N potassium;triethyl(oxido)silane Chemical compound [K+].CC[Si]([O-])(CC)CC YTJYCWNMRAYWLV-UHFFFAOYSA-N 0.000 description 1
- LBKJNHPKYFYCLL-UHFFFAOYSA-N potassium;trimethyl(oxido)silane Chemical compound [K+].C[Si](C)(C)[O-] LBKJNHPKYFYCLL-UHFFFAOYSA-N 0.000 description 1
- SMPFVXSGKBDYLS-UHFFFAOYSA-N potassium;triphenylmethanolate Chemical group [K+].C=1C=CC=CC=1C(C=1C=CC=CC=1)([O-])C1=CC=CC=C1 SMPFVXSGKBDYLS-UHFFFAOYSA-N 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- DKVXCZLIQTYMTQ-UHFFFAOYSA-N sodium triphenylmethanolate Chemical group C1(=CC=CC=C1)C([O-])(C1=CC=CC=C1)C1=CC=CC=C1.[Na+] DKVXCZLIQTYMTQ-UHFFFAOYSA-N 0.000 description 1
- FENAEJZLLDFTSY-UHFFFAOYSA-N sodium;(4-methoxyphenyl)methanolate Chemical compound [Na+].COC1=CC=C(C[O-])C=C1 FENAEJZLLDFTSY-UHFFFAOYSA-N 0.000 description 1
- OZSKVIDRCKBITI-UHFFFAOYSA-M sodium;2-bromophenolate Chemical compound [Na+].[O-]C1=CC=CC=C1Br OZSKVIDRCKBITI-UHFFFAOYSA-M 0.000 description 1
- GQFIWFPBDXSASA-UHFFFAOYSA-M sodium;2-chlorophenolate Chemical compound [Na+].[O-]C1=CC=CC=C1Cl GQFIWFPBDXSASA-UHFFFAOYSA-M 0.000 description 1
- JEWWMBHOAYPNNU-UHFFFAOYSA-M sodium;2-formylphenolate Chemical compound [Na+].[O-]C1=CC=CC=C1C=O JEWWMBHOAYPNNU-UHFFFAOYSA-M 0.000 description 1
- ONFAAMBUOAGWSG-UHFFFAOYSA-M sodium;2-methylphenolate Chemical compound [Na+].CC1=CC=CC=C1[O-] ONFAAMBUOAGWSG-UHFFFAOYSA-M 0.000 description 1
- ZLUZHXGLNFCZPR-UHFFFAOYSA-M sodium;3,4-dichlorophenolate Chemical compound [Na+].[O-]C1=CC=C(Cl)C(Cl)=C1 ZLUZHXGLNFCZPR-UHFFFAOYSA-M 0.000 description 1
- NSKZUZIVFLCFTE-UHFFFAOYSA-M sodium;3,4-dimethoxyphenolate Chemical compound [Na+].COC1=CC=C([O-])C=C1OC NSKZUZIVFLCFTE-UHFFFAOYSA-M 0.000 description 1
- PDRMAMGSHFDLIV-UHFFFAOYSA-M sodium;3,4-dimethylphenolate Chemical compound [Na+].CC1=CC=C([O-])C=C1C PDRMAMGSHFDLIV-UHFFFAOYSA-M 0.000 description 1
- JWYMWHGENDPLFG-UHFFFAOYSA-M sodium;3-chlorophenolate Chemical compound [Na+].[O-]C1=CC=CC(Cl)=C1 JWYMWHGENDPLFG-UHFFFAOYSA-M 0.000 description 1
- WHRAMHWTLGRJHH-UHFFFAOYSA-M sodium;3-formylphenolate Chemical compound [Na+].[O-]C1=CC=CC(C=O)=C1 WHRAMHWTLGRJHH-UHFFFAOYSA-M 0.000 description 1
- QOINKMNRLBCJOP-UHFFFAOYSA-M sodium;3-methylphenolate Chemical compound [Na+].CC1=CC=CC([O-])=C1 QOINKMNRLBCJOP-UHFFFAOYSA-M 0.000 description 1
- BJJASZZTNHTBNH-UHFFFAOYSA-M sodium;4-(dimethylamino)phenolate Chemical compound [Na+].CN(C)C1=CC=C([O-])C=C1 BJJASZZTNHTBNH-UHFFFAOYSA-M 0.000 description 1
- OTIRLXNYGIORBW-UHFFFAOYSA-M sodium;4-bromophenolate Chemical compound [Na+].[O-]C1=CC=C(Br)C=C1 OTIRLXNYGIORBW-UHFFFAOYSA-M 0.000 description 1
- CFPLEOLETMZLIB-UHFFFAOYSA-M sodium;4-chlorophenolate Chemical compound [Na+].[O-]C1=CC=C(Cl)C=C1 CFPLEOLETMZLIB-UHFFFAOYSA-M 0.000 description 1
- JJVBULRLWIXXNC-UHFFFAOYSA-M sodium;4-formylphenolate Chemical compound [Na+].[O-]C1=CC=C(C=O)C=C1 JJVBULRLWIXXNC-UHFFFAOYSA-M 0.000 description 1
- ZECBPBHBGNLLMU-UHFFFAOYSA-M sodium;4-methylphenolate Chemical compound [Na+].CC1=CC=C([O-])C=C1 ZECBPBHBGNLLMU-UHFFFAOYSA-M 0.000 description 1
- NHMRUJXVSXNWJZ-UHFFFAOYSA-N sodium;adamantan-1-olate Chemical group [Na+].C1C(C2)CC3CC2CC1([O-])C3 NHMRUJXVSXNWJZ-UHFFFAOYSA-N 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- HIFJOEJCXUJQBO-UHFFFAOYSA-N sodium;cyclohexanolate Chemical group [Na+].[O-]C1CCCCC1 HIFJOEJCXUJQBO-UHFFFAOYSA-N 0.000 description 1
- SLQXUIRYBQDRRB-UHFFFAOYSA-N sodium;cyclopentanolate Chemical group [Na+].[O-]C1CCCC1 SLQXUIRYBQDRRB-UHFFFAOYSA-N 0.000 description 1
- LFQULJPVXNYWAG-UHFFFAOYSA-N sodium;phenylmethanolate Chemical group [Na]OCC1=CC=CC=C1 LFQULJPVXNYWAG-UHFFFAOYSA-N 0.000 description 1
- FGSPLJPSYLRWCI-UHFFFAOYSA-N sodium;triethyl(oxido)silane Chemical compound [Na+].CC[Si]([O-])(CC)CC FGSPLJPSYLRWCI-UHFFFAOYSA-N 0.000 description 1
- HSNUIYJWTSJUMS-UHFFFAOYSA-N sodium;trimethyl(oxido)silane Chemical compound [Na+].C[Si](C)(C)[O-] HSNUIYJWTSJUMS-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- ZGBNKNOAADXGOH-UHFFFAOYSA-N tert-butyl 4-bromoindole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)C=CC2=C1Br ZGBNKNOAADXGOH-UHFFFAOYSA-N 0.000 description 1
- PBWDRTGTQIXVBR-UHFFFAOYSA-N tert-butyl 5-bromoindole-1-carboxylate Chemical compound BrC1=CC=C2N(C(=O)OC(C)(C)C)C=CC2=C1 PBWDRTGTQIXVBR-UHFFFAOYSA-N 0.000 description 1
- CLMZYPRKIYEXFB-UHFFFAOYSA-N tert-butyl-dimethyl-phenoxysilane Chemical group CC(C)(C)[Si](C)(C)OC1=CC=CC=C1 CLMZYPRKIYEXFB-UHFFFAOYSA-N 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WVMSIBFANXCZKT-UHFFFAOYSA-N triethyl(hydroxy)silane Chemical compound CC[Si](O)(CC)CC WVMSIBFANXCZKT-UHFFFAOYSA-N 0.000 description 1
- OJAJJFGMKAZGRZ-UHFFFAOYSA-N trimethyl(phenoxy)silane Chemical group C[Si](C)(C)OC1=CC=CC=C1 OJAJJFGMKAZGRZ-UHFFFAOYSA-N 0.000 description 1
- AAPLIUHOKVUFCC-UHFFFAOYSA-N trimethylsilanol Chemical compound C[Si](C)(C)O AAPLIUHOKVUFCC-UHFFFAOYSA-N 0.000 description 1
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyridine Compounds (AREA)
Description
【0001】
【発明に属する技術分野】
本発明は芳香族性エーテルの製造方法に関するものである。さらに詳しくは、トリ(ターシャリーブチル)ホスフィンとパラジウム化合物からなる触媒を用いる芳香族性エーテルの製造方法に関する。芳香族性エーテル類は、医薬、農薬の中間体として、また液晶素材として、更にはフェノール誘導体の前駆体として有用な化合物である。
【0002】
【従来の技術】
従来、アリールエーテルの合成としては、化学量論量のアルコキシ銅化合物とハロゲン化ベンゼン類を用い、ジメチルホルムアミド等の極性溶媒下実施する方法が知られている(Journal of American Chemical Society,1974年,96巻,2829−2835.)。しかしながらこの方法は、多量の銅廃棄物が生成することや高価な溶媒を使用する等、環境的にも経済的にも好ましい方法ではなかった。
【0003】
また最近では、パラジウム又はニッケル触媒と、ビス(ジフェニルホスフィノ)ビナフチル(BINAP)や1,1’−ビス(ジフェニルホスフィノ)フェロセン等の2座ホスフィンを用いて、アリールハライドとアルコキサイドからアリールエーテルを合成する方法が報告されている(Journal of American Chemical Society,1997年,119巻,3395−3396.及びJournal of Organic Chemistry,1997年,62巻,5413−5418.)。しかしながらこの方法も、基質として電子吸引性基を有するアリールハライド類や多環縮合アリールブロマイドを使用した場合にのみに有効であり、また触媒量も多く必要とすることから、応用性が乏しく、実用的にはまだ不充分であった。
【0004】
【発明が解決しようとする課題】
本発明者らは、上記課題を解決するため鋭意検討を行った結果、トリ(ターシャリーブチル)ホスフィンとパラジウム化合物を必須成分とする触媒を使用することにより芳香族性エーテルを高活性、高選択的に合成できることを見出し本発明を完成するに至った。
【0005】
即ち本発明は、トリ(ターシャリーブチル)ホスフィンとパラジウム化合物を必須成分とする触媒存在下、下記一般式(1)
ArXn (1)
(式中、Arは置換若しくは無置換のアリール基、窒素、酸素及び硫黄からなる群より選ばれる少なくとも1種のヘテロ原子を有する置換若しくは無置換のヘテロアリール基、又は置換若しくは無置換のフェロセニル基を表し、Xは塩素、臭素、ヨウ素又はフッ素を表し、nは1〜6の範囲の整数を表す。)で示される化合物と下記一般式(2)
ROM (2)
(式中、Rは炭素数1〜20のアルキル基、置換若しくは無置換のアリール基、又は炭素数3〜10のトリアルキルシリル基を表し、Mはアルカリ金属を表す。)で示される化合物を反応させることを特徴とする下記一般式(4)
Ar−(O−R)m (4)
(式中、Arは一般式(1)のArと同一定義であり、Rは一般式(2)のRと同一定義であり、mは1〜3の範囲の整数を表す。)で示される芳香族性エーテルの製造方法、並びに
トリ(ターシャリーブチル)ホスフィンとパラジウム化合物を必須成分とする触媒存在下、下記一般式(1)
ArXn (1)
(式中、Arは置換若しくは無置換のアリール基、窒素、酸素及び硫黄からなる群より選ばれる少なくとも1種のヘテロ原子を有する置換若しくは無置換のヘテロアリール基、又は置換若しくは無置換のフェロセニル基を表し、Xは塩素、臭素、ヨウ素又はフッ素を表し、nは1〜6の範囲の整数を表す。)で示される化合物、下記一般式(3)
ROH (3)
(式中、Rは炭素数1〜20のアルキル基、置換若しくは無置換のアリール基、又は炭素数3〜10のトリアルキルシリル基を表す。)で示される化合物及び塩基を反応させることを特徴とする下記一般式(4)
Ar−(O−R)m (4)
(式中、Arは一般式(1)のArと同一定義であり、Rは一般式(3)のRと同一定義であり、mは1〜3の範囲の整数を表す。)で示される芳香族性エーテルの製造方法である。
【0006】
以下、本発明を更に詳細に説明する。
【0007】
本発明においては、パラジウム化合物とトリ(ターシャリーブチル)ホスフィンが必須であり、両者を組み合わせて触媒として反応系に加える。添加方法は、反応系にそれぞれ単独に加えても、予め錯体の形に調製して添加してもよい。
【0008】
本発明において、パラジウム化合物としては特に限定するものではないが、例えば、ヘキサクロロパラジウム(IV)酸ナトリウム四水和物、ヘキサクロロパラジウム(IV)酸カリウム等の4価のパラジウム化合物、塩化パラジウム(II)、臭化パラジウム(II)、酢酸パラジウム(II)、パラジウムアセチルアセトナート(II)、ジクロロビス(ベンゾニトリル)パラジウム(II)、ジクロロビス(アセトニトリル)パラジウム(II)、ジクロロビス(トリフェニルホスフィン)パラジウム(II)、ジクロロテトラアンミンパラジウム(II)、ジクロロ(シクロオクタ−1,5−ジエン)パラジウム(II)、パラジウムトリフルオロアセテート(II)等の2価パラジウム化合物、トリス(ジベンジリデンアセトン)二パラジウム(0)、トリス(ジベンジリデンアセトン)二パラジウムクロロホルム錯体(0)、テトラキス(トリフェニルホスフィン)パラジウム(0)等の0価パラジウム化合物を挙げることができる。これらのうち、特に好ましくは、酢酸パラジウムである。パラジウム化合物の使用量は、特に限定するものではないが、上記一般式(1)で示される化合物に対し、パラジウム換算で0.01〜20.0モル%であり、より好ましくは、パラジウム換算で0.1〜10.0モル%である。
【0009】
本発明において、トリ(ターシャリーブチル)ホスフィンの使用量は特に限定するものではないが、パラジウム化合物に対して0.5〜10倍モルの範囲が適当であり、より好ましくはパラジウム化合物に対して0.8〜5倍モルの範囲である。
【0010】
本発明において、上記一般式(1)で示される化合物は、置換若しくは無置換のアリールハライド、窒素、酸素及び硫黄からなる群より選ばれる少なくとも1種のヘテロ原子を有する置換若しくは無置換のヘテロアリールハライド、又は置換若しくは無置換のフェロセニルハライドであり、これらの芳香族性基に直接結合したハライド数は1〜6の間で任意に選ぶことができる。
【0011】
置換又は無置換アリールハライドの具体的な例としては、ブロモベンゼン、クロロベンゼン、ヨードベンゼン、フルオロベンゼン等の無置換アリールハライド;o−ブロモトルエン,m−ブロモトルエン,p−ブロモトルエン、o−クロロトルエン,m−クロロトルエン,p−クロロトルエン、o−(t−ブチル)ブロモベンゼン,m−(t−ブチル)ブロモベンゼン,p−(t−ブチル)ブロモベンゼン、5−ブロモ−1,2,4−トリメチルベンゼン、2−ブロモ−m−キシレン、2−ブロモ−p−キシレン、3−ブロモ−o−キシレン、4−ブロモ−o−キシレン、4−ブロモ−m−キシレン、5−ブロモ−m−キシレン、2−クロロ−m−キシレン、2−クロロ−p−キシレン、3−クロロ−o−キシレン、4−クロロ−o−キシレン、4−クロロ−m−キシレン、5−クロロ−m−キシレン、5−クロロ−1,2,4−トリメチルベンゼン、5−ブロモ−1,2,4−トリメチルベンゼン、o−ヨードトルエン,m−ヨードトルエン,p−ヨードトルエン、p−(2−ブロモエチル)ブロモベンゼン、p−(2−ブロモエチル)クロロベンゼン、m−(2−ブロモエチル)ブロモベンゼン等のアルキル置換アリールハライド類;o−ブロモベンズアルデヒド,m−ブロモベンズアルデヒド,p−ブロモベンズアルデヒド、o−クロロベンズアルデヒド,m−クロロベンズアルデヒド,p−クロロベンズアルデヒド、o−フルオロベンズアルデヒド,m−フルオロベンズアルデヒド,p−フルオロベンズアルデヒド、o−ブロモベンゾトリフルオリド,m−ブロモベンゾトリフルオリド,p−ブロモベンゾトリフルオリド、o−クロロベンゾトリフルオリド,m−クロロベンゾトリフルオリド,p−クロロベンゾトリフルオリド、o−ブロモベンゾニトリル,m−ブロモベンゾニトリル,p−ブロモベンゾニトリル、4−クロロベンゾフェノン、1−ブロモ−3−(トリフルオロメトキシ)ベンゼン、1−ブロモ−4−(トリフルオロメトキシ)ベンゼン、1−クロロ−3−(トリフルオロメトキシ)ベンゼン、1−クロロ−4−(トリフルオロメトキシ)ベンゼン、o−ジブロモベンゼン,m−ジブロモベンゼン,p−ジブロモベンゼン、o−ジクロロベンゼン,m−ジクロロベンゼン,p−ジクロロベンゼン、o−ブロモフルオロベンゼン,m−ブロモフルオロベンゼン,p−ブロモフルオロベンゼン、o−ブロモクロロベンゼン,m−ブロモクロロベンゼン,p−ブロモクロロベンゼン、o−クロロフルオロベンゼン,m−クロロフルオロベンゼン,p−クロロフルオロベンゼン、2−ブロモ−4−フルオロトルエン、2−ブロモ−5−フルオロトルエン、3−ブロモ−4−フルオロトルエン、4−ブロモ−2−フルオロトルエン、4−ブロモ−3−フルオロトルエン、2−ブロモ−5−クロロトルエン、3−ブロモ−4−クロロベンゾトリフルオリド、5−ブロモ−2−クロロベンゾトリフルオリド、1−ブロモ−2,3−ジクロロベンゼン、1−ブロモ−2,6−ジクロロベンゼン、1−ブロモ−3,5−ジクロロベンゼン、1,3,5−トリブロモベンゼン、1,3,5−トリクロロベンゼン、1,3,5−トリヨードベンゼン等の電子吸引性官能基を有するアリールハライド類;o−ブロモアニソール,m−ブロモアニソール,p−ブロモアニソール、1−ブロモ−2,5−ジメトキシベンゼン、1−ブロモ−3,4−ジメトキシベンゼン、1−ブロモ−2,3−ジメトキシベンゼン、o−ブロモフェノール,m−ブロモフェノール,p−ブロモフェノール、o−ヨードフェノール,m−ヨードフェノール,p−ヨードフェノール、o−クロロアニソール,m−クロロアニソール,p−クロロアニソール、o−ヨードアニソール,m−ヨードアニソール,p−ヨードアニソール、4−ブロモ−1,2−(メチレンジオキシ)ベンゼン、3−ブロモ−1,2−(メチレンジオキシ)ベンゼン、4−クロロ−1,2−(メチレンジオキシ)ベンゼン、4−ブロモ−1,2−(エチレンジオキシ)ベンゼン、3−ブロモ−1,2−(エチレンジオキシ)ベンゼン、4−クロロ−1,2−(エチレンジオキシ)ベンゼン、2−クロロフェネチルアルコール、3−クロロフェネチルアルコール、4−クロロフェネチルアルコール、2−ブロモフェネチルアルコール、3−ブロモフェネチルアルコール、4−ブロモフェネチルアルコール、o−(N,N−ジメチル)ブロモアニリン,m−(N,N−ジメチル)ブロモアニリン,p−(N,N−ジメチル)ブロモアニリン、o−(N,N−ジエチル)ブロモアニリン,m−(N,N−ジエチル)ブロモアニリン,p−(N,N−ジエチル)ブロモアニリン、p−ブロモスチレン、m−ブロモスチレン、p−クロロスチレン等の電子供与性官能基を有するアリールハライド類;1−ブロモナフタレン、2−ブロモナフタレン、1−ブロモ−2−メチルナフタレン、1−ブロモ−4−メチルナフタレン、1−クロロナフタレン、2−クロロナフタレン、1−クロロ−2−メチルナフタレン、1−クロロ−4−メチルナフタレン、7−ブロモ−2−ナフタレンアルデヒド、4−ブロモ−1−ナフタレンアルデヒド、7−ブロモ−1−ナフタレンアルデヒド、7−クロロ−2−ナフタレンアルデヒド、2−ブロモ−1−ナフタレンアルデヒド、1−ブロモアントラセン、9,10−ジブロモアントラセン、9,10−ジクロロアントラセン等の多環縮合アリールハライド類;2−ブロモビフェニル、3−ブロモビフェニル、4−ブロモビフェニル、2−クロロビフェニル、3−クロロビフェニル、4−クロロビフェニル、4,4’−ジブロモビフェニル、4,4’−ジクロロビフェニル、4,4’−ジヨードビフェニル、トリス(4−ブロモフェニル)アミン、1,3,5−トリス(4−ブロモフェニル)ベンゼン等の多環アリールハライド類等を挙げることができる。
【0012】
窒素、酸素及び硫黄からなる群より選ばれる少なくとも1種のヘテロ原子を有する置換又は無置換のヘテロアリールハライドの具体例としては、2−ブロモピリジン、3−ブロモピリジン、4−ブロモピリジン、3−クロロピリジン、2−クロロピリジン、3−ヨードピリジン、2−ブロモ−4−トリフルオロメチルピリジン、2−クロロ−4−トリフルオロメチルピリジン、4−ブロモキノリン、3−ブロモキノリン、4−クロロキノリン、1−(トリメチルシリル)−2−ブロモピロール、2−ブロモピロール、1−(トリメチルシリル)−3−ブロモピロール、3−ブロモピロール、4−ホルミル−2−ブロモピロール、2−クロロピロール、2−ブロモフラン、3−ブロモフラン、4−ブロモベンゾフラン、5−ブロモベンゾフラン、4−クロロベンゾフラン、2−ブロモチオフェン、3−ブロモチオフェン、4−ブロモベンゾチオフェン、3−ブロモベンゾチオフェン、4−クロロベンゾチオフェン、1−ベンジル−2−ブロモインドール、1−ベンジル−4−ブロモインドール、1−ベンジル−5−ブロモインドール、1−(ターシャリーブトキシカルボニル)−4−ブロモインドール、1−(ターシャリーブトキシカルボニル)−5−ブロモインドール、2−ブロモインドール、2−クロロインドール、4−ブロモインドール、5−ブロモインドール、1−(ベンジル)−3−ブロモカルバゾール、1−(ターシャリーブトキシカルボニル)−3−ブロモカルバゾール、3−ブロモカルバゾール等が挙げることができる。
【0013】
置換又は無置換のフェロセニルハライドの具体例としては、ブロモフェロセン、ヨードフェロセン、クロロフェロセン、1,1’−ジブロモフェロセン、1,1’−ジヨードフェロセン、1−(ジメチルアミノメチル)−2−ブロモフェロセン、1−(ジメチルアミノメチル)−2−ヨードフェロセン、1−(1−ジメチルアミノエチル)−2−ブロモフェロセン、1−(1−ジメチルアミノエチル)−2−ヨードフェロセン、1−(ジフェニルホスフィノメチル)−2−ブロモフェロセン、1−(ジフェニルホスフィノメチル)−2−ヨードフェロセン、1−(1−ジフェニルホスフィノエチル)−2−ブロモフェロセン、1−(1−ジフェニルホスフィノエチル)−2−ヨードフェロセン、1−(ジメチルホスフィノメチル)−2−ブロモフェロセン、1−(ジメチルホスフィノメチル)−2−ヨードフェロセン、1−(1−ジメチルホスフィノエチル)−2−ブロモフェロセン、1−(1−ジメチルホスフィノエチル)−2−ヨードフェロセン、1−(ジフェニルホスフィノメチル)−1’−ブロモフェロセン、1−(ジフェニルホスフィノメチル)−1’−ヨードフェロセン、1−(ジメチルホスフィノメチル)−1’−ヨードフェロセン、1−(1−ジフェニルホスフィノエチル)−1’−ブロモフェロセン、1−(1−ジフェニルホスフィノエチル)−1’−ヨードフェロセン等を挙げることができる。
【0014】
上記一般式(1)で示される化合物が不斉炭素を有する場合には、ラセミ体又は光学活性体のどちらであっても良い。
【0015】
本発明の方法は、上記一般式(1)で示されるこれらの化合物の中でも、置換若しくは無置換のアリールハライド、又は窒素、酸素及び硫黄からなる群より選ばれる少なくとも1種のヘテロ原子を有する置換若しくは無置換のヘテロアリールハライドに対して特に好ましく適用される。
【0016】
本発明において、上記一般式(2)で示される化合物は、炭素数1〜20のアルコキシアルカリ金属化合物、無置換若しくは置換アリールオキシアルカリ金属化合物、又は炭素数3〜10のトリアルキルシロキシアルカリ金属化合物である。
【0017】
炭素数1〜20のアルコキシアルカリ金属化合物の具体例としては、メトキシナトリウム、メトキシカリウム、メトキシリチウム、エトキシナトリウム、n−ブトキシナトリウム、ターシャリーブトキシナトリウム、ターシャリーブトキシカリウム、ターシャリーブトキシリチウム、ベンジルオキシナトリウム、ベンジルオキシカリウム、シクロペンチルオキシナトリウム、シクロヘキシルオキシナトリウム、1−アダマンチルオキシナトリウム、1−アダマンチルオキシリチウム、トリフェニルメトキシナトリウム、トリフェニルメトキシカリウム、トリフェニルメトキシリチウム、メントキシナトリウム、メントキシリチウム等を挙げることができ、これらのうち特に好ましくはターシャリーブトキシナトリウムである。
【0018】
置換又は無置換のアリールオキシアルカリ金属化合物の具体例としては、フェノキシナトリウム、フェノキシカリウム、フェノキシリチウム、o−トリルオキシナトリウム,m−トリルオキシナトリウム,p−トリルオキシナトリウム、o−トリルオキシカリウム,m−トリルオキシカリウム,p−トリルオキシカリウム、o−トリルオキシリチウム,m−トリルオキシリチウム,p−トリルオキシリチウム、o−アニソオキシナトリウム,m−アニソオキシナトリウム,p−アニソオキシナトリウム、o−アニソオキシカリウム,m−アニソオキシカリウム,p−アニソオキシカリウム、o−アニソオキシリチウム,m−アニソオキシリチウム,p−アニソオキシリチウム、o−ジメチルアミノフェノキシナトリウム,m−ジメチルアミノフェノキシナトリウム,p−ジメチルアミノフェノキシナトリウム、o−ジメチルアミノフェノキシカリウム,m−ジメチルアミノフェノキシカリウム,p−ジメチルアミノフェノキシカリウム、o−ジメチルアミノフェノキシリチウム,m−ジメチルアミノフェノキシリチウム,p−ジメチルアミノフェノキシリチウム、o−ホルミルフェノキシナトリウム,m−ホルミルフェノキシナトリウム,p−ホルミルフェノキシナトリウム、o−ホルミルフェノキシカリウム,m−ホルミルフェノキシカリウム,p−ホルミルフェノキシカリウム、o−ホルミルフェノキシリチウム,m−ホルミルフェノキシリチウム,p−ホルミルフェノキシリチウム、o−ブロモフェノキシナトリウム,m−ブロモフェノキシナトリウム,p−ブロモフェノキシナトリウム、o−ブロモフェノキシカリウム,m−ブロモフェノキシカリウム,p−ブロモフェノキシカリウム、o−ブロモフェノキシリチウム,m−ブロモフェノキシリチウム,p−ブロモフェノキシリチウム、o−クロロフェノキシナトリウム,m−クロロフェノキシナトリウム,p−クロロフェノキシナトリウム、o−クロロフェノキシカリウム,m−クロロフェノキシカリウム,p−クロロフェノキシカリウム、o−クロロフェノキシリチウム,m−クロロフェノキシリチウム,p−クロロフェノキシリチウム、o−ピペラジニルフェノキシナトリウム,m−ピペラジニルフェノキシナトリウム,p−ピペラジニルフェノキシナトリウム、3,4−ジメチルフェノキシナトリウム、3,4−ジメチルフェノキシカリウム、3,4,5−トリメチルフェノキシナトリウム、3,4−ジクロロフェノキシナトリウム、3,4−ジメトキシフェノキシナトリウム、p−ハイドロキノンモノナトリウム塩、p−ハイドロキノンモノカリウム塩、1−ナフトキシナトリウム、1−ナフトキシカリウム、2−ナフトキシナトリウム、2−ナフトキシカリウム、2−ナフトキシリチウム、1−メトキシ−2−ナフトキシナトリウム、2−メトキシ−1−ナフトキシナトリウム、2−ブロモ−1−ナフトキシナトリウム、2−メチル−1−ナフトキシナトリウム、4−ビフェノキシナトリウム、3−ビフェノキシナトリウム、2−ビフェノキシナトリウム、1,1’−ビナフト−2,2’−オールモノナトリウム塩等を挙げることができる。
【0019】
炭素数3〜10のトリアルキルシロキシアルカリ金属化合物の具体例としては、トリメチルシロキシナトリウム、トリメチルシロキシカリウム、トリメチルシロキシリチウム、トリエチルシロキシナトリウム、トリエチルシロキシカリウム、トリエチルシロキシリチウム、(ターシャリーブチル)ジメチルシロキシナトリウム、(ターシャリーブチル)ジメチルシロキシカリウム、(ターシャリーブチル)ジメチルシロキシリチウム等を挙げることができる。上記一般式(2)で示される化合物の使用量は、上記一般式(1)で示される化合物に対してモル比で通常0.6〜5.0の範囲であり、より好ましくは0.8〜2.0の範囲である。
【0020】
本発明において、上記一般式(3)で示される化合物としては、炭素数1〜20のアルコールや、置換若しくは無置換のフェノール誘導体、炭素数3〜10のトリアルキルシラノールが例示される。
【0021】
炭素数1〜20のアルコールの具体例としては、メタノール、エタノール、n−ブタノール、ターシャリーブタノール、ベンジルアルコール、シクロペンタノール、シクロヘキサノール、1−アダマンタンオール、トリフェニルメタノール、メントール等を挙げることができる。
【0022】
置換又は無置換のフェノール誘導体の具体例としては、フェノール、o−クレゾール,m−クレゾール,p−クレゾール、o−メトキシフェノール,m−メトキシフェノール,p−メトキシフェノール、o−ジメチルアミノフェノール,m−ジメチルアミノフェノール,p−ジメチルアミノフェノール、o−ヒドロキシベンズアルデヒド,m−ヒドロキシベンズアルデヒド,p−ヒドロキシベンズアルデヒド、o−ブロモフェノール,m−ブロモフェノール,p−ブロモフェノール、o−クロロフェノール,m−クロロフェノール,p−クロロフェノール、o−ピペラジニルフェノール,m−ピペラジニルフェノール,p−ピペラジニルフェノール、3,4−ジメチルフェノール、3,4−ジメチルフェノール、3,4,5−トリメチルフェノール、3,4−ジクロロフェノール、3,4−ジメトキシフェノール、p−ハイドロキノン、1−ナフトール、2−ナフトール、1−メトキシ−2−ナフトール、2−メトキシ−1−ナフトール、2−ブロモ−1−ナフトール、2−メチル−1−ナフトール、4−ビフェノール、3−ビフェノール、2−ビフェノール、1,1’−ビナフト−2,2’−オール等を挙げることができる。
【0023】
炭素数3〜10のトリアルキルシラノールの具体例としては、トリメチルシラノール、トリエチルシラノール、ターシャリーブチルジメチルシラノール等を挙げることができる。
【0024】
上記一般式(3)で示される化合物の使用量は一般式(1)のArXnに対してモル比で通常0.6〜5.0の範囲であり、より好ましくは0.8〜2.0である。
【0025】
本発明において、上記一般式(3)で示される化合物とともに使用される塩基としては、無機塩基及び有機塩基からなる群より選択すればよく、特に限定するものではないが、より好ましくは、水素化ナトリウム、水素化カリウム、水素化リチウム、ナトリウムアミド、カリウムアミド、リチウムアミド、炭酸カリウム、炭酸ナトリウム、炭酸リチウム、炭酸セシウム、炭酸水素カリウム、炭酸水素ナトリウム、ナトリウム金属、カリウム金属、リチウム金属、メトキシナトリウム、メトキシカリウム、エトキシナトリウム、エトキシカリウム、エトキシリチウム、ターシャリーブトキシリチウム、ターシャリーブトキシナトリウム、ターシャリーブトキシカリウム等を具体例として挙げることができる。
【0026】
これらの塩基の使用量は上記一般式(3)で示される化合物に対してモル比で通常0.6〜3.0の範囲であり、より好ましくは0.8〜2.0の範囲である。
【0027】
本発明における反応は、通常は不活性溶媒下に実施される。使用できる溶媒としては、本反応を著しく阻害しない溶媒であればよく、特に限定するものではないが、ベンゼン、トルエン、キシレン等の芳香族炭化水素溶媒、ジエチルエーテル、テトラヒドロフラン、ジオキサン等のエーテル溶媒、アセトニトリル、ジメチルホルムアミド、ジメチルスルホキシド、ヘキサメチルホスホトリアミド等を例示することができる。より好ましくは、ベンゼン、トルエン、キシレン等の芳香族炭化水素溶媒である。
【0028】
本発明は、常圧下、窒素、アルゴン等の不活性ガス雰囲気下に実施されるが、加圧条件下に実施することもできる。
【0029】
本発明は、反応温度20℃〜300℃の範囲で実施されるが、より好ましくは50℃〜200℃の範囲である。
【0030】
反応時間は、反応条件、ArXn、及びパラジウム化合物により異なるが、数分乃至は72時間の範囲から選択すればよい。
【0031】
反応終了後、常法に従い処理することにより目的とする化合物を得ることができる。
【0032】
本発明で製造することのできる上記一般式(4)で示される芳香族性エーテルは、上記一般式(1)で示される化合物と上記一般式(2)で示される化合物、又は上記一般式(1)で示される化合物、上記一般式(3)で示される化合物及び塩基を反応させることによって得られるものであり、特に限定するものではないが、具体例としては以下のものを挙げることができる。即ち、ターシャリーブトキシベンゼン、トリメチルシロキシベンゼン、(ターシャリーブチルジメチルシロキシ)ベンゼン、o−(ターシャリーブトキシ)トルエン,m−(ターシャリーブトキシ)トルエン,p−(ターシャリーブトキシ)トルエン、o−(ターシャリーブトキシ)ターシャリーブチルベンゼン,m−(ターシャリーブトキシ)ターシャリーブチルベンゼン,p−(ターシャリーブトキシ)ターシャリーブチルベンゼン、2−(ターシャリーブトキシ)−p−キシレン、5−(ターシャリーブトキシ)−1,2,4−トリメチルベンゼン、o−ターシャリーブトキシベンズアルデヒド,m−ターシャリーブトキシベンズアルデヒド,p−ターシャリーブトキシベンズアルデヒド、o−ベンジルオキシベンズアルデヒド,m−ベンジルオキシベンズアルデヒド,p−ベンジルオキシベンズアルデヒド、o−(ターシャリーブチルジメチルシロキシベンズアルデヒド,m−(ターシャリーブチルジメチルシロキシベンズアルデヒド,p−(ターシャリーブチルジメチルシロキシベンズアルデヒド、o−トリメチルシロキシベンズアルデヒド,m−トリメチルシロキシベンズアルデヒド,p−トリメチルシロキシベンズアルデヒド、o−(ターシャリーブトキシ)トリフルオロメチルベンゼン,m−(ターシャリーブトキシ)トリフルオロメチルベンゼン,p−(ターシャリーブトキシ)トリフルオロメチルベンゼン、o−(ターシャリーブトキシ)トリフルオロメトキシベンゼン,m−(ターシャリーブトキシ)トリフルオロメトキシベンゼン,p−(ターシャリーブトキシ)トリフルオロメトキシベンゼン、o−(ターシャリーブトキシ)ブロモベンゼン,m−(ターシャリーブトキシ)ブロモベンゼン,p−(ターシャリーブトキシ)ブロモベンゼン、o−(ターシャリーブトキシ)クロロベンゼン,m−(ターシャリーブトキシ)クロロベンゼン,p−(ターシャリーブトキシ)クロロベンゼン、o−(ターシャリーブトキシ)フルオロベンゼン,m−(ターシャリーブトキシ)フルオロベンゼン,p−(ターシャリーブトキシ)フルオロベンゼン、o−(フェノキシ)フルオロベンゼン,m−(フェノキシ)フルオロベンゼン,p−(フェノキシ)フルオロベンゼン、o−(ターシャリーブチルジメチルシロキシ)ブロモベンゼン,m−(ターシャリーブチルジメチルシロキシ)ブロモベンゼン,p−(ターシャリーブチルジメチルシロキシ)ブロモベンゼン、3−(ターシャリーブトキシ)−4−フルオロトルエン、1−(ターシャリーブトキシ)−3,5−ジクロロベンゼン、1,2−ビス(ターシャリーブトキシ)ベンゼン、1,3−ビス(ターシャリーブトキシ)ベンゼン、1,4−ビス(ターシャリーブトキシ)ベンゼン、1,3,5−トリス(ターシャリーブトキシ)ベンゼン、4−(ターシャリーブトキシ)ベンゾフェノン、4−(ターシャリーブチルジメチルシロキシ)ベンゾフェノン、4−(フェノキシ)ベンゾフェノン、o−(ターシャリーブトキシ)ベンゾニトリル,m−(ターシャリーブトキシ)ベンゾニトリル,p−(ターシャリーブトキシ)ベンゾニトリル、o−(ターシャリーブトキシ)アニソール,m−(ターシャリーブトキシ)アニソール,p−(ターシャリーブトキシ)アニソール、4−ターシャリーブトキシ−1,2−ジメトキシベンゼン、3−ターシャリーブトキシ−1,2−ジメトキシベンゼン、4−ターシャリーブトキシ−1,2−(メチレンジオキシ)ベンゼン、4−トリメチルシロキシ−1,2−(メチレンジオキシ)ベンゼン、4−ターシャリーブチルジメチルシロキシ−1,2−(メチレンジオキシ)ベンゼン、3−ターシャリーブトキシ−1,2−(メチレンジオキシ)ベンゼン、4−ターシャリーブトキシ−1,2−(エチレンジオキシ)ベンゼン、4−トリメチルシロキシ−1,2−(エチレンジオキシ)ベンゼン、4−ターシャリーブチルジメチルシロキシ−1,2−(エチレンジオキシ)ベンゼン、3−ターシャリーブトキシ−1,2−(エチレンジオキシ)ベンゼン、4−(ターシャリーブトキシ)フェネチルアルコール、o−(ターシャリーブトキシ)−N,N−ジメチルアニリン,m−(ターシャリーブトキシ)−N,N−ジメチルアニリン,p−(ターシャリーブトキシ)−N,N−ジメチルアニリン、1−ターシャリーブトキシナフタレン、2−ターシャリブトキシナフタレン、1−ターシャリーブトキシ−4−メチルナフタレン、7−ターシャリーブトキシ−2−ナフタレンアルデヒド、1−タシャリーブトキシアントラセン、4−タシャリーブトキシビフェニル、3−ターシャリーブトキシビフェニル、4,4’−ビス(ターシャリーブトキシ)ビフェニル、4,4’−ビス(ターシャリーブチルジメチルシロキシ)ビフェニル、トリス(4−ターシャリーブトキシフェニル)アミン、1,3,5−トリス(4−ターシャリーブトキシフェニル)ベンゼン、2−(ターシャリブトキシ)ピリジン、3−(ターシャリブトキシ)ピリジン、4−(ターシャリブトキシ)ピリジン、5−トリフルオロメチル−2−(ターシャリーブトキシ)ピリジン、4−(ターシャリーブトキシ)キノリン、3−(ターシャリーブトキシ)ピロール、1−トリメチルシリル−3−(ターシャリーブトキシ)ピロール、3−(ターシャリーブトキシ)フラン、4−(ターシャリーブトキシ)ベンゾフラン、3−(ターシャリーブトキシ)チオフェン、4−(ターシャリーブトキシ)ベンゾチオフェン、1−ベンジル−4−(ターシャリーブトキシ)インドール、1−ベンジル−5−(ターシャリーブトキシ)インドール、4−(ターシャリーブトキシ)インドール、1−(ターシャリーブトキシカルボニル)−4−(ターシャリーブトキシ)インドール、1−ベンジル−3−(ターシャリーブトキシ)カルバゾール、ターシャリーブトキシフェロセン、1,1’−ジ(ターシャリーブトキシ)フェロセン、1−(ジメチルアミノメチル)−2−(ターシャリーブトキシ)フェロセン、1−(1−ジメチルアミノエチル)−2−(ターシャリーブトキシ)フェロセン、1−(ジフェニルホスフィノメチル)−2−(ターシャリーブトキシ)フェロセン、1−(1−ジフェニルホスフィノエチル)−2−(ターシャリーブトキシ)フェロセン、1−(1−ジフェニルホスフィノエチル)−2−メトキシフェロセン、1−(ジメチルアミノメチル)−1’−(ターシャリーブトキシ)フェロセン、1−(1−ジメチルアミノエチル)−1’−(ターシャリーブトキシ)フェロセン、1−(ジフェニルホスフィノメチル)−1’−(ターシャリーブトキシ)フェロセン、1−(1−ジフェニルホスフィノエチル)−1’−(ターシャリーブトキシ)フェロセン、1−(1−ジフェニルホスフィノエチル)−1’−メトキシフェロセン、1−(2−ブロモエチル)−4−(ターシャリーブトキシ)ベンゼン、1−(2−ブロモエチル)−3−(ターシャリーブトキシ)ベンゼン、p−(ターシャリーブトキシ)スチレン、m−(ターシャリーブトキシ)スチレン等を挙げることができる。これらは、不斉炭素を有する場合にはラセミ体又は光学活性体のどちらであっても良い。
【0033】
【発明の効果】
本発明により、医薬、農薬の中間体として、また液晶素材として、更にはフェノール誘導体の前駆体として有用な芳香族性エーテルを、パラジウム化合物とトリ(ターシャリーブチル)ホスフィンを必須成分とする触媒の存在下、電子吸引性基から電子供与性基を有する幅広い基質から、高活性・高選択的に合成することが可能となった。
【0034】
【実施例】
以下に本発明の実施例を示すが、本発明はこれらに限定されるものではない。
【0035】
実施例1
温度計、3方コック、撹拌子を備えた30ml3口フラスコを窒素置換し、酢酸パラジウム(和光純薬製、12.9mg,0.0575mmol,基質ブロモベンゼンに対して1.0mol%)、ターシャリーブトキシナトリウム620.3mg(6.45mmol)、o−キシレン8ml、ブロモベンゼン905mg(5.76mmol)、トリ(ターシャリーブチル)ホスフィン(関東化学製)の41.3mg/ml o−キシレン溶液0.85ml(35.1mg,0.173mmol,パラジウムに対して3.0倍モル)の順番に加えた。15分間要して120℃まで昇温した後、120℃で2時間撹拌した。その後室温まで冷却後、水10mlを投入し、ジエチルエーテルで抽出した。内部標準物質としてアニソール650mgを加え、ガスクロマトグラフィーで定量分析を行った。ターシャリーブトキシベンゼンの収率は81.4%で、他にベンゼンが1.2%、ビフェニルが2.4%生成していた。
【0036】
ガスクロマトグラフィー分析条件
カラム :OV−1 0.32mmID×60m
キャリアガス :窒素 1.0ml/分
インジェクション温度 :300℃
ディテクター温度 :300℃
カラム温度 :60℃(9分間)→昇温10℃/分→300℃
実施例2〜実施例10
表1に示した基質及び反応時間を用いた以外は実施例1と同様な操作を繰り返した。
【0037】
【表1】
【0038】
実施例11、実施例12
表2に示した基質及び反応時間を用いた以外は実施例1と同様な操作を繰り返した。
【0039】
【表2】
【0040】
比較例1
トリ(ターシャリーブチル)ホスフィンの代わりに、1,1’−ジフェニルホスフィノフェロセン(パラジウムに対し2倍モル)を用い、反応時間を20時間としたこと以外は実施例1と同じ操作を繰り返した。ターシャリーブトキシベンゼンの収率は6%であった。[0001]
[Technical field belonging to the invention]
The present invention relates to a method for producing an aromatic ether. More specifically, the present invention relates to a method for producing an aromatic ether using a catalyst comprising tri (tertiary butyl) phosphine and a palladium compound. Aromatic ethers are useful compounds as intermediates for pharmaceuticals and agricultural chemicals, as liquid crystal materials, and as precursors for phenol derivatives.
[0002]
[Prior art]
Conventionally, as a method for synthesizing aryl ethers, a method in which a stoichiometric amount of an alkoxy copper compound and a halogenated benzene are used and a polar solvent such as dimethylformamide is used is known (Journal of American Chemical Society, 1974, 96, 2829-2835.). However, this method is not an environmentally and economically preferable method because a large amount of copper waste is generated and an expensive solvent is used.
[0003]
In recent years, aryl ethers can be converted from aryl halides and alkoxides using palladium or nickel catalysts and bidentate phosphines such as bis (diphenylphosphino) binaphthyl (BINAP) and 1,1′-bis (diphenylphosphino) ferrocene. Methods for synthesis have been reported (Journal of American Chemical Society, 1997, 119, 3395-3396. And Journal of Organic Chemistry, 1997, 62, 5413-5418.). However, this method is also effective only when an aryl halide having an electron-withdrawing group or a polycyclic fused aryl bromide is used as a substrate, and also requires a large amount of catalyst. It was still inadequate.
[0004]
[Problems to be solved by the invention]
As a result of intensive studies to solve the above problems, the inventors of the present invention have high activity and high selection of aromatic ethers by using a catalyst having tri (tertiary butyl) phosphine and a palladium compound as essential components. As a result, the present invention was completed.
[0005]
That is, the present invention provides the following general formula (1) in the presence of a catalyst having tri (tertiary butyl) phosphine and a palladium compound as essential components.
ArX n (1)
(Wherein Ar represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having at least one heteroatom selected from the group consisting of nitrogen, oxygen and sulfur, or a substituted or unsubstituted ferrocenyl group X represents chlorine, bromine, iodine or fluorine, and n represents an integer in the range of 1 to 6.) and the following general formula (2)
ROM (2)
(Wherein R represents an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group, or a trialkylsilyl group having 3 to 10 carbon atoms, and M represents an alkali metal). The following general formula (4) characterized by reacting
Ar- (O-R) m (4)
(In the formula, Ar has the same definition as Ar in the general formula (1), R has the same definition as R in the general formula (2), and m represents an integer in the range of 1 to 3). A method for producing aromatic ethers, and
In the presence of a catalyst having tri (tertiary butyl) phosphine and a palladium compound as essential components, the following general formula (1)
ArX n (1)
(Wherein Ar represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having at least one heteroatom selected from the group consisting of nitrogen, oxygen and sulfur, or a substituted or unsubstituted ferrocenyl group X represents chlorine, bromine, iodine or fluorine, and n represents an integer in the range of 1 to 6, and the following general formula (3)
ROH (3)
(In the formula, R represents an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group, or a trialkylsilyl group having 3 to 10 carbon atoms. To express . And a base represented by the following general formula (4):
Ar- (O-R) m (4)
(In the formula, Ar has the same definition as Ar in the general formula (1), R has the same definition as R in the general formula (3), and m represents an integer in the range of 1 to 3). This is a method for producing an aromatic ether.
[0006]
Hereinafter, the present invention will be described in more detail.
[0007]
In the present invention, a palladium compound and tri (tertiary butyl) phosphine are essential, and both are combined and added to the reaction system as a catalyst. The addition method may be added individually to the reaction system or may be prepared in the form of a complex in advance.
[0008]
In the present invention, the palladium compound is not particularly limited, and examples thereof include tetravalent palladium compounds such as sodium hexachloropalladium (IV) tetrahydrate, potassium hexachloropalladium (IV), and palladium (II) chloride. , Palladium (II) bromide, palladium (II) acetate, palladium acetylacetonate (II), dichlorobis (benzonitrile) palladium (II), dichlorobis (acetonitrile) palladium (II), dichlorobis (triphenylphosphine) palladium (II) ), Dichlorotetraamminepalladium (II), dichloro (cycloocta-1,5-diene) palladium (II), divalent palladium compounds such as palladium trifluoroacetate (II), tris (dibenzylideneacetone) Palladium (0), tris (dibenzylideneacetone) dipalladium chloroform complex (0), it may be mentioned tetrakis (triphenylphosphine) palladium (0) 0-valent palladium compounds such as. Of these, palladium acetate is particularly preferable. Although the usage-amount of a palladium compound is not specifically limited, It is 0.01-20.0 mol% in conversion of palladium with respect to the compound shown by the said General formula (1), More preferably, it is conversion of palladium It is 0.1-10.0 mol%.
[0009]
In the present invention, the amount of tri (tertiary butyl) phosphine used is not particularly limited, but a range of 0.5 to 10 moles relative to the palladium compound is appropriate, and more preferably relative to the palladium compound. It is the range of 0.8-5 times mole.
[0010]
In the present invention, the compound represented by the general formula (1) is a substituted or unsubstituted heteroaryl having at least one heteroatom selected from the group consisting of a substituted or unsubstituted aryl halide, nitrogen, oxygen and sulfur. It is a halide or a substituted or unsubstituted ferrocenyl halide, and the number of halides directly bonded to these aromatic groups can be arbitrarily selected between 1 and 6.
[0011]
Specific examples of the substituted or unsubstituted aryl halide include unsubstituted aryl halides such as bromobenzene, chlorobenzene, iodobenzene, and fluorobenzene; o-bromotoluene, m-bromotoluene, p-bromotoluene, o-chlorotoluene. , M-chlorotoluene, p-chlorotoluene, o- (t-butyl) bromobenzene, m- (t-butyl) bromobenzene, p- (t-butyl) bromobenzene, 5-bromo-1,2,4 -Trimethylbenzene, 2-bromo-m-xylene, 2-bromo-p-xylene, 3-bromo-o-xylene, 4-bromo-o-xylene, 4-bromo-m-xylene, 5-bromo-m- Xylene, 2-chloro-m-xylene, 2-chloro-p-xylene, 3-chloro-o-xylene, 4-chloro-o-xylene 4-chloro-m-xylene, 5-chloro-m-xylene, 5-chloro-1,2,4-trimethylbenzene, 5-bromo-1,2,4-trimethylbenzene, o-iodotoluene, m- Alkyl-substituted aryl halides such as iodotoluene, p-iodotoluene, p- (2-bromoethyl) bromobenzene, p- (2-bromoethyl) chlorobenzene, m- (2-bromoethyl) bromobenzene; o-bromobenzaldehyde, m -Bromobenzaldehyde, p-bromobenzaldehyde, o-chlorobenzaldehyde, m-chlorobenzaldehyde, p-chlorobenzaldehyde, o-fluorobenzaldehyde, m-fluorobenzaldehyde, p-fluorobenzaldehyde, o-bromobenzotrifluoride, m-bromobenzoto Fluoride, p-bromobenzotrifluoride, o-chlorobenzotrifluoride, m-chlorobenzotrifluoride, p-chlorobenzotrifluoride, o-bromobenzonitrile, m-bromobenzonitrile, p-bromobenzonitrile, 4- Chlorobenzophenone, 1-bromo-3- (trifluoromethoxy) benzene, 1-bromo-4- (trifluoromethoxy) benzene, 1-chloro-3- (trifluoromethoxy) benzene, 1-chloro-4- (tri Fluoromethoxy) benzene, o-dibromobenzene, m-dibromobenzene, p-dibromobenzene, o-dichlorobenzene, m-dichlorobenzene, p-dichlorobenzene, o-bromofluorobenzene, m-bromofluorobenzene, p-bromo Fluorobenzene, o-bu Lomochlorobenzene, m-bromochlorobenzene, p-bromochlorobenzene, o-chlorofluorobenzene, m-chlorofluorobenzene, p-chlorofluorobenzene, 2-bromo-4-fluorotoluene, 2-bromo-5-fluorotoluene, 3 -Bromo-4-fluorotoluene, 4-bromo-2-fluorotoluene, 4-bromo-3-fluorotoluene, 2-bromo-5-chlorotoluene, 3-bromo-4-chlorobenzotrifluoride, 5-bromo- 2-chlorobenzotrifluoride, 1-bromo-2,3-dichlorobenzene, 1-bromo-2,6-dichlorobenzene, 1-bromo-3,5-dichlorobenzene, 1,3,5-tribromobenzene, Electron attraction of 1,3,5-trichlorobenzene, 1,3,5-triiodobenzene, etc. Aryl halides having a functional group; o-bromoanisole, m-bromoanisole, p-bromoanisole, 1-bromo-2,5-dimethoxybenzene, 1-bromo-3,4-dimethoxybenzene, 1-bromo-2 , 3-dimethoxybenzene, o-bromophenol, m-bromophenol, p-bromophenol, o-iodophenol, m-iodophenol, p-iodophenol, o-chloroanisole, m-chloroanisole, p-chloroanisole O-iodoanisole, m-iodoanisole, p-iodoanisole, 4-bromo-1,2- (methylenedioxy) benzene, 3-bromo-1,2- (methylenedioxy) benzene, 4-chloro- 1,2- (methylenedioxy) benzene, 4-bromo-1,2- (ethylene Oxy) benzene, 3-bromo-1,2- (ethylenedioxy) benzene, 4-chloro-1,2- (ethylenedioxy) benzene, 2-chlorophenethyl alcohol, 3-chlorophenethyl alcohol, 4-chlorophenethyl Alcohol, 2-bromophenethyl alcohol, 3-bromophenethyl alcohol, 4-bromophenethyl alcohol, o- (N, N-dimethyl) bromoaniline, m- (N, N-dimethyl) bromoaniline, p- (N, N -Dimethyl) bromoaniline, o- (N, N-diethyl) bromoaniline, m- (N, N-diethyl) bromoaniline, p- (N, N-diethyl) bromoaniline, p-bromostyrene, m-bromo Aryl halides having an electron-donating functional group such as styrene and p-chlorostyrene; 1-bromo Naphthalene, 2-bromonaphthalene, 1-bromo-2-methylnaphthalene, 1-bromo-4-methylnaphthalene, 1-chloronaphthalene, 2-chloronaphthalene, 1-chloro-2-methylnaphthalene, 1-chloro-4- Methylnaphthalene, 7-bromo-2-naphthalenealdehyde, 4-bromo-1-naphthalenealdehyde, 7-bromo-1-naphthalenealdehyde, 7-chloro-2-naphthalenealdehyde, 2-bromo-1-naphthalenealdehyde, 1- Polycyclic fused aryl halides such as bromoanthracene, 9,10-dibromoanthracene, 9,10-dichloroanthracene; 2-bromobiphenyl, 3-bromobiphenyl, 4-bromobiphenyl, 2-chlorobiphenyl, 3-chlorobiphenyl, 4-chlorobiphenyl, 4,4'-dibu Polycyclic aryl halides such as lomobiphenyl, 4,4′-dichlorobiphenyl, 4,4′-diiodobiphenyl, tris (4-bromophenyl) amine, 1,3,5-tris (4-bromophenyl) benzene Etc.
[0012]
Specific examples of the substituted or unsubstituted heteroaryl halide having at least one heteroatom selected from the group consisting of nitrogen, oxygen and sulfur include 2-bromopyridine, 3-bromopyridine, 4-bromopyridine, 3- Chloropyridine, 2-chloropyridine, 3-iodopyridine, 2-bromo-4-trifluoromethylpyridine, 2-chloro-4-trifluoromethylpyridine, 4-bromoquinoline, 3-bromoquinoline, 4-chloroquinoline, 1- (trimethylsilyl) -2-bromopyrrole, 2-bromopyrrole, 1- (trimethylsilyl) -3-bromopyrrole, 3-bromopyrrole, 4-formyl-2-bromopyrrole, 2-chloropyrrole, 2-bromofuran, 3-bromofuran, 4-bromobenzofuran, 5-bromobenzofuran 4-chlorobenzofuran, 2-bromothiophene, 3-bromothiophene, 4-bromobenzothiophene, 3-bromobenzothiophene, 4-chlorobenzothiophene, 1-benzyl-2-bromoindole, 1-benzyl-4-bromoindole 1-benzyl-5-bromoindole, 1- (tertiarybutoxycarbonyl) -4-bromoindole, 1- (tertiarybutoxycarbonyl) -5-bromoindole, 2-bromoindole, 2-chloroindole, 4- Examples thereof include bromoindole, 5-bromoindole, 1- (benzyl) -3-bromocarbazole, 1- (tertiary butoxycarbonyl) -3-bromocarbazole, 3-bromocarbazole and the like.
[0013]
Specific examples of the substituted or unsubstituted ferrocenyl halide include bromoferrocene, iodoferrocene, chloroferrocene, 1,1′-dibromoferrocene, 1,1′-diiodoferrocene, 1- (dimethylaminomethyl) -2. -Bromoferrocene, 1- (dimethylaminomethyl) -2-iodoferrocene, 1- (1-dimethylaminoethyl) -2-bromoferrocene, 1- (1-dimethylaminoethyl) -2-iodoferrocene, 1- ( Diphenylphosphinomethyl) -2-bromoferrocene, 1- (diphenylphosphinomethyl) -2-iodoferrocene, 1- (1-diphenylphosphinoethyl) -2-bromoferrocene, 1- (1-diphenylphosphinoethyl) ) -2-Iodoferrocene, 1- (dimethylphosphinomethyl) -2-bromo Erocene, 1- (dimethylphosphinomethyl) -2-iodoferrocene, 1- (1-dimethylphosphinoethyl) -2-bromoferrocene, 1- (1-dimethylphosphinoethyl) -2-iodoferrocene, 1- (Diphenylphosphinomethyl) -1′-bromoferrocene, 1- (diphenylphosphinomethyl) -1′-iodoferrocene, 1- (dimethylphosphinomethyl) -1′-iodoferrocene, 1- (1-diphenylphos (Finoethyl) -1′-bromoferrocene, 1- (1-diphenylphosphinoethyl) -1′-iodoferrocene and the like.
[0014]
When the compound represented by the general formula (1) has an asymmetric carbon, it may be a racemate or an optically active substance.
[0015]
Among these compounds represented by the general formula (1), the method of the present invention is a substituted or unsubstituted aryl halide, or a substitution having at least one heteroatom selected from the group consisting of nitrogen, oxygen and sulfur. Alternatively, it is particularly preferably applied to unsubstituted heteroaryl halides.
[0016]
In the present invention, the compound represented by the general formula (2) is an alkoxy alkali metal compound having 1 to 20 carbon atoms, an unsubstituted or substituted aryloxyalkali metal compound, or a trialkylsiloxy alkali metal compound having 3 to 10 carbon atoms. It is.
[0017]
Specific examples of the alkoxy alkali metal compound having 1 to 20 carbon atoms include methoxy sodium, methoxy potassium, methoxy lithium, ethoxy sodium, n-butoxy sodium, tertiary butoxy sodium, tertiary butoxy potassium, tertiary butoxy lithium, benzyloxy Sodium, benzyloxy potassium, cyclopentyloxy sodium, cyclohexyloxy sodium, 1-adamantyloxy sodium, 1-adamantyloxy lithium, triphenylmethoxy sodium, triphenylmethoxy potassium, triphenylmethoxy lithium, menthoxy sodium, menthoxy lithium, etc. Of these, tertiary butoxy sodium is particularly preferable.
[0018]
Specific examples of the substituted or unsubstituted aryloxyalkali metal compounds include phenoxy sodium, phenoxy potassium, phenoxy lithium, o-tolyloxy sodium, m-tolyloxy sodium, p-tolyloxy sodium, o-tolyloxy potassium, m. -Tolyloxypotassium, p-tolyloxypotassium, o-tolyloxylithium, m-tolyloxylithium, p-tolyloxylithium, o-anisooxysodium, m-anisooxysodium, p-anisooxysodium, o-aniso Oxypotassium, m-anisoxypotassium, p-anisoxypotassium, o-anisoxylithium, m-anisoxylithium, p-anisoxylithium, o-dimethylaminophenoxysodium, m-dimethylamino Enoxysodium, p-dimethylaminophenoxysodium, o-dimethylaminophenoxypotassium, m-dimethylaminophenoxypotassium, p-dimethylaminophenoxypotassium, o-dimethylaminophenoxylithium, m-dimethylaminophenoxylithium, p-dimethyl Aminophenoxy lithium, o-formylphenoxy sodium, m-formylphenoxy sodium, p-formylphenoxy sodium, o-formylphenoxy potassium, m-formylphenoxy potassium, p-formylphenoxy potassium, o-formylphenoxy lithium, m-formylphenoxy Lithium, p-formylphenoxy lithium, o-bromophenoxy sodium, m-bromophenoxy sodium, p-bromophenoxy Sodium, o-bromophenoxy potassium, m-bromophenoxy potassium, p-bromophenoxy potassium, o-bromophenoxy lithium, m-bromophenoxy lithium, p-bromophenoxy lithium, o-chlorophenoxy sodium, m-chlorophenoxy sodium, p-chlorophenoxy sodium, o-chlorophenoxy potassium, m-chlorophenoxy potassium, p-chlorophenoxy potassium, o-chlorophenoxy lithium, m-chlorophenoxy lithium, p-chlorophenoxy lithium, o-piperazinylphenoxy sodium, m-piperazinylphenoxy sodium, p-piperazinylphenoxy sodium, 3,4-dimethylphenoxy sodium, 3,4-dimethylphenoxy potassium, 3,4,5 -Trimethylphenoxy sodium, 3,4-dichlorophenoxy sodium, 3,4-dimethoxyphenoxy sodium, p-hydroquinone monosodium salt, p-hydroquinone monopotassium salt, 1-naphthoxy sodium, 1-naphthoxy potassium, 2-naphtho Sodium xoxy, 2-naphthoxy potassium, 2-naphthoxy lithium, 1-methoxy-2-naphthoxy sodium, 2-methoxy-1-naphthoxy sodium, 2-bromo-1-naphthoxy sodium, 2-methyl-1 Examples thereof include naphthoxy sodium, 4-biphenoxy sodium, 3-biphenoxy sodium, 2-biphenoxy sodium, 1,1′-binaphth-2,2′-ol monosodium salt and the like.
[0019]
Specific examples of the trialkylsiloxy alkali metal compound having 3 to 10 carbon atoms include trimethylsiloxy sodium, trimethylsiloxy potassium, trimethylsiloxy lithium, triethylsiloxy sodium, triethylsiloxy potassium, triethylsiloxylithium, (tertiary butyl) dimethylsiloxy sodium (Tertiary butyl) dimethylsiloxy potassium, (tertiary butyl) dimethyl siloxy lithium, and the like. The usage-amount of the compound shown by the said General formula (2) is the range of 0.6-5.0 normally by molar ratio with respect to the compound shown by the said General formula (1), More preferably, it is 0.8. It is in the range of ~ 2.0.
[0020]
In the present invention, examples of the compound represented by the general formula (3) include alcohols having 1 to 20 carbon atoms, substituted or unsubstituted phenol derivatives, and trialkylsilanols having 3 to 10 carbon atoms.
[0021]
Specific examples of the alcohol having 1 to 20 carbon atoms include methanol, ethanol, n-butanol, tertiary butanol, benzyl alcohol, cyclopentanol, cyclohexanol, 1-adamantanol, triphenylmethanol, menthol and the like. it can.
[0022]
Specific examples of the substituted or unsubstituted phenol derivative include phenol, o-cresol, m-cresol, p-cresol, o-methoxyphenol, m-methoxyphenol, p-methoxyphenol, o-dimethylaminophenol, m- Dimethylaminophenol, p-dimethylaminophenol, o-hydroxybenzaldehyde, m-hydroxybenzaldehyde, p-hydroxybenzaldehyde, o-bromophenol, m-bromophenol, p-bromophenol, o-chlorophenol, m-chlorophenol, p-chlorophenol, o-piperazinylphenol, m-piperazinylphenol, p-piperazinylphenol, 3,4-dimethylphenol, 3,4-dimethylphenol, 3,4,5-trimethylphenol 3,4-dichlorophenol, 3,4-dimethoxyphenol, p-hydroquinone, 1-naphthol, 2-naphthol, 1-methoxy-2-naphthol, 2-methoxy-1-naphthol, 2-bromo-1 -Naphthol, 2-methyl-1-naphthol, 4-biphenol, 3-biphenol, 2-biphenol, 1,1'-binaphth-2,2'-ol and the like can be mentioned.
[0023]
Specific examples of the trialkylsilanol having 3 to 10 carbon atoms include trimethylsilanol, triethylsilanol, tertiary butyldimethylsilanol and the like.
[0024]
The amount of the compound represented by the general formula (3) used is ArX in the general formula (1). n The molar ratio is usually in the range of 0.6 to 5.0, more preferably 0.8 to 2.0.
[0025]
In the present invention, the base used together with the compound represented by the general formula (3) may be selected from the group consisting of inorganic bases and organic bases, and is not particularly limited, but more preferably hydrogenation. Sodium, potassium hydride, lithium hydride, sodium amide, potassium amide, lithium amide, potassium carbonate, sodium carbonate, lithium carbonate, cesium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, sodium metal, potassium metal, lithium metal, methoxy sodium Specific examples include methoxy potassium, ethoxy sodium, ethoxy potassium, ethoxy lithium, tertiary butoxy lithium, tertiary butoxy sodium, and tertiary butoxy potassium.
[0026]
The amount of these bases to be used is usually in the range of 0.6 to 3.0, more preferably in the range of 0.8 to 2.0, in terms of molar ratio with respect to the compound represented by the general formula (3). .
[0027]
The reaction in the present invention is usually carried out in an inert solvent. Solvents that can be used are not particularly limited as long as they do not significantly inhibit this reaction, and are not particularly limited, but are aromatic hydrocarbon solvents such as benzene, toluene and xylene, ether solvents such as diethyl ether, tetrahydrofuran and dioxane, Acetonitrile, dimethylformamide, dimethyl sulfoxide, hexamethylphosphotriamide and the like can be exemplified. More preferred are aromatic hydrocarbon solvents such as benzene, toluene and xylene.
[0028]
The present invention is carried out under an atmospheric pressure and an inert gas atmosphere such as nitrogen and argon, but can also be carried out under pressurized conditions.
[0029]
Although this invention is implemented in the range of reaction temperature 20 degreeC-300 degreeC, More preferably, it is the range of 50 degreeC-200 degreeC.
[0030]
The reaction time is the reaction conditions, ArX n And depending on the palladium compound, it may be selected from a range of several minutes to 72 hours.
[0031]
After completion of the reaction, the desired compound can be obtained by treatment according to a conventional method.
[0032]
The aromatic ether represented by the general formula (4) that can be produced in the present invention is a compound represented by the general formula (1) and a compound represented by the general formula (2), or the general formula ( Although it is obtained by reacting the compound represented by 1), the compound represented by the above general formula (3) and a base, and is not particularly limited, the following can be mentioned as specific examples. . That is, tertiary butoxybenzene, trimethylsiloxybenzene, (tertiarybutyldimethylsiloxy) benzene, o- (tertiarybutoxy) toluene, m- (tertiarybutoxy) toluene, p- (tertiarybutoxy) toluene, o- ( Tertiary butoxy) tertiary butyl benzene, m- (tertiary butoxy) tertiary butyl benzene, p- (tertiary butoxy) tertiary butyl benzene, 2- (tertiary butoxy) -p-xylene, 5- (tertiary Butoxy) -1,2,4-trimethylbenzene, o-tert-butoxybenzaldehyde, m-tert-butoxybenzaldehyde, p-tert-butoxybenzaldehyde, o-benzyloxybenzaldehyde, m- N-oxylbenzaldehyde, p-benzyloxybenzaldehyde, o- (tertiarybutyldimethylsiloxybenzaldehyde, m- (tertiarybutyldimethylsiloxybenzaldehyde, p- (tertiarybutyldimethylsiloxybenzaldehyde), o-trimethylsiloxybenzaldehyde, m-trimethyl Siloxybenzaldehyde, p-trimethylsiloxybenzaldehyde, o- (tertiarybutoxy) trifluoromethylbenzene, m- (tertiarybutoxy) trifluoromethylbenzene, p- (tertiarybutoxy) trifluoromethylbenzene, o- (tertiary) Butoxy) trifluoromethoxybenzene, m- (tertiary butoxy) trifluoromethoxybenzene, p- (tertiary rib) Xyl) trifluoromethoxybenzene, o- (tertiarybutoxy) bromobenzene, m- (tertiarybutoxy) bromobenzene, p- (tertiarybutoxy) bromobenzene, o- (tertiarybutoxy) chlorobenzene, m- (tersia) Lieboxy) chlorobenzene, p- (tertiarybutoxy) chlorobenzene, o- (tertiarybutoxy) fluorobenzene, m- (tertiarybutoxy) fluorobenzene, p- (tertiarybutoxy) fluorobenzene, o- (phenoxy) fluoro Benzene, m- (phenoxy) fluorobenzene, p- (phenoxy) fluorobenzene, o- (tertiarybutyldimethylsiloxy) bromobenzene, m- (tertiarybutyldimethylsiloxy) bromobenzene, p- (Tertiarybutyldimethylsiloxy) bromobenzene, 3- (tertiarybutoxy) -4-fluorotoluene, 1- (tertiarybutoxy) -3,5-dichlorobenzene, 1,2-bis (tertiarybutoxy) benzene, 1,3-bis (tertiarybutoxy) benzene, 1,4-bis (tertiarybutoxy) benzene, 1,3,5-tris (tertiarybutoxy) benzene, 4- (tertiarybutoxy) benzophenone, 4- ( Tert-butyldimethylsiloxy) benzophenone, 4- (phenoxy) benzophenone, o- (tertiarybutoxy) benzonitrile, m- (tertiarybutoxy) benzonitrile, p- (tertiarybutoxy) benzonitrile, o- (tertiary) Butoxy) anisole, m- ( -Tert-butoxy) anisole, p- (tert-butoxy) anisole, 4-tert-butoxy-1,2-dimethoxybenzene, 3-tert-butoxy-1,2-dimethoxybenzene, 4-tert-butoxy-1,2- -(Methylenedioxy) benzene, 4-trimethylsiloxy-1,2- (methylenedioxy) benzene, 4-tertiarybutyldimethylsiloxy-1,2- (methylenedioxy) benzene, 3-tertiarybutoxy-1 , 2- (methylenedioxy) benzene, 4-tertiarybutoxy-1,2- (ethylenedioxy) benzene, 4-trimethylsiloxy-1,2- (ethylenedioxy) benzene, 4-tertiarybutyldimethylsiloxy -1,2- (ethylenedioxy) benzene, 3-tarsha -Butoxy-1,2- (ethylenedioxy) benzene, 4- (tertiarybutoxy) phenethyl alcohol, o- (tertiarybutoxy) -N, N-dimethylaniline, m- (tertiarybutoxy) -N, N- Dimethylaniline, p- (tertiary butoxy) -N, N-dimethylaniline, 1-tertiary butoxynaphthalene, 2-tertiary butoxynaphthalene, 1-tertiary butoxy-4-methylnaphthalene, 7-tertiary butoxy-2 -Naphthalene aldehyde, 1-tert-butoxyanthracene, 4-tert-butoxybiphenyl, 3-tert-butoxybiphenyl, 4,4'-bis (tertiarybutoxy) biphenyl, 4,4'-bis (tertiary butyldimethylsiloxy) ) Biphenyl, Tris (4 Tertiary butoxyphenyl) amine, 1,3,5-tris (4-tertiarybutoxyphenyl) benzene, 2- (tertiarybutoxy) pyridine, 3- (tertiarybutoxy) pyridine, 4- (tertiarybutoxy) pyridine , 5-trifluoromethyl-2- (tertiarybutoxy) pyridine, 4- (tertiarybutoxy) quinoline, 3- (tertiarybutoxy) pyrrole, 1-trimethylsilyl-3- (tertiarybutoxy) pyrrole, 3- ( Tertiary butoxy) furan, 4- (tertiary butoxy) benzofuran, 3- (tertiary butoxy) thiophene, 4- (tertiary butoxy) benzothiophene, 1-benzyl-4- (tertiary butoxy) indole, 1-benzyl -5- (Tertiary buttoki ) Indole, 4- (tertiarybutoxy) indole, 1- (tertiarybutoxycarbonyl) -4- (tertiarybutoxy) indole, 1-benzyl-3- (tertiarybutoxy) carbazole, tertiary butoxyferrocene, 1, 1′-di (tertiarybutoxy) ferrocene, 1- (dimethylaminomethyl) -2- (tertiarybutoxy) ferrocene, 1- (1-dimethylaminoethyl) -2- (tertiarybutoxy) ferrocene, 1- ( Diphenylphosphinomethyl) -2- (tertiarybutoxy) ferrocene, 1- (1-diphenylphosphinoethyl) -2- (tertiarybutoxy) ferrocene, 1- (1-diphenylphosphinoethyl) -2-methoxyferrocene , 1- (dimethylaminomethyl) -1 ′ (Tertiarybutoxy) ferrocene, 1- (1-dimethylaminoethyl) -1 ′-(tertiarybutoxy) ferrocene, 1- (diphenylphosphinomethyl) -1 ′-(tertiarybutoxy) ferrocene, 1- (1 -Diphenylphosphinoethyl) -1 '-(tertiarybutoxy) ferrocene, 1- (1-diphenylphosphinoethyl) -1'-methoxyferrocene, 1- (2-bromoethyl) -4- (tertiarybutoxy) benzene 1- (2-bromoethyl) -3- (tertiarybutoxy) benzene, p- (tertiarybutoxy) styrene, m- (tertiarybutoxy) styrene, and the like. These may be racemic or optically active when they have asymmetric carbons.
[0033]
【The invention's effect】
According to the present invention, an aromatic ether useful as an intermediate for pharmaceuticals and agricultural chemicals, as a liquid crystal material, and further as a precursor of a phenol derivative, a catalyst containing palladium compounds and tri (tertiary butyl) phosphine as essential components. In the presence, it has become possible to synthesize highly active and highly selective from a wide range of substrates having electron-withdrawing groups from electron-withdrawing groups.
[0034]
【Example】
Examples of the present invention are shown below, but the present invention is not limited thereto.
[0035]
Example 1
A 30 ml three-necked flask equipped with a thermometer, three-way cock and stir bar was replaced with nitrogen, palladium acetate (manufactured by Wako Pure Chemicals, 12.9 mg, 0.0575 mmol, 1.0 mol% with respect to the substrate bromobenzene), and tertiary. 620.3 mg (6.45 mmol) of sodium butoxy, 8 ml of o-xylene, 905 mg (5.76 mmol) of bromobenzene, 0.85 ml of 41.3 mg / ml o-xylene solution of tri (tertiary butyl) phosphine (manufactured by Kanto Chemical) (35.1 mg, 0.173 mmol, 3.0-fold moles with respect to palladium). After 15 minutes, the temperature was raised to 120 ° C., followed by stirring at 120 ° C. for 2 hours. Then, after cooling to room temperature, 10 ml of water was added and extracted with diethyl ether. 650 mg of anisole was added as an internal standard substance, and quantitative analysis was performed by gas chromatography. The yield of tertiary butoxybenzene was 81.4%. In addition, 1.2% of benzene and 2.4% of biphenyl were produced.
[0036]
Gas chromatography analysis conditions
Column: OV-1 0.32 mm ID x 60 m
Carrier gas: Nitrogen 1.0 ml / min
Injection temperature: 300 ° C
Detector temperature: 300 ° C
Column temperature: 60 ° C. (9 minutes) → temperature increase 10 ° C./min→300° C.
Example 2 to Example 10
The same operation as in Example 1 was repeated except that the substrate and reaction time shown in Table 1 were used.
[0037]
[Table 1]
[0038]
Example 11 and Example 12
The same operation as in Example 1 was repeated except that the substrates and reaction times shown in Table 2 were used.
[0039]
[Table 2]
[0040]
Comparative Example 1
Instead of tri (tertiary butyl) phosphine, 1,1′-diphenylphosphinoferrocene (2 times mole with respect to palladium) was used, and the same operation as in Example 1 was repeated except that the reaction time was 20 hours. . The yield of tertiary butoxybenzene was 6%.
Claims (4)
ArXn (1)
(式中、Arは置換若しくは無置換のアリール基、窒素、酸素及び硫黄からなる群より選ばれる少なくとも1種のヘテロ原子を有する置換若しくは無置換のヘテロアリール基、又は置換若しくは無置換のフェロセニル基を表し、Xは塩素、臭素、ヨウ素又はフッ素を表し、nは1〜6の範囲の整数を表す。)で示される化合物と下記一般式(2)
ROM (2)
(式中、Rは炭素数1〜20のアルキル基、置換若しくは無置換のアリール基、又は炭素数3〜10のトリアルキルシリル基を表し、Mはアルカリ金属を表す。)で示される化合物を反応させることを特徴とする下記一般式(4)
Ar−(O−R)m (4)
(式中、Arは一般式(1)のArと同一定義であり、Rは一般式(2)のRと同一定義であり、mは1〜3の範囲の整数を表す。)で示される芳香族性エーテルの製造方法。In the presence of a catalyst having tri (tertiary butyl) phosphine and a palladium compound as essential components, the following general formula (1)
ArX n (1)
(Wherein Ar represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having at least one heteroatom selected from the group consisting of nitrogen, oxygen and sulfur, or a substituted or unsubstituted ferrocenyl group X represents chlorine, bromine, iodine or fluorine, and n represents an integer in the range of 1 to 6.) and the following general formula (2)
ROM (2)
(Wherein R represents an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group, or a trialkylsilyl group having 3 to 10 carbon atoms, and M represents an alkali metal). The following general formula (4) characterized by reacting
Ar- (O-R) m (4)
(In the formula, Ar has the same definition as Ar in the general formula (1), R has the same definition as R in the general formula (2), and m represents an integer in the range of 1 to 3). A method for producing an aromatic ether.
ArXn (1)
(式中、Arは置換若しくは無置換のアリール基、窒素、酸素及び硫黄からなる群より選ばれる少なくとも1種のヘテロ原子を有する置換若しくは無置換のヘテロアリール基、又は置換若しくは無置換のフェロセニル基を表し、Xは塩素、臭素、ヨウ素又はフッ素を表し、nは1〜6の範囲の整数を表す。)で示される化合物、下記一般式(3)
ROH (3)
(式中、Rは炭素数1〜20のアルキル基、置換若しくは無置換のアリール基、又は炭素数3〜10のトリアルキルシリル基を表す。)で示される化合物及び塩基を反応させることを特徴とする下記一般式(4)
Ar−(O−R)m (4)
(式中、Arは一般式(1)のArと同一定義であり、Rは一般式(3)のRと同一定義であり、mは1〜3の範囲の整数を表す。)で示される芳香族性エーテルの製造方法。In the presence of a catalyst having tri (tertiary butyl) phosphine and a palladium compound as essential components, the following general formula (1)
ArX n (1)
(Wherein Ar represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having at least one heteroatom selected from the group consisting of nitrogen, oxygen and sulfur, or a substituted or unsubstituted ferrocenyl group X represents chlorine, bromine, iodine or fluorine, and n represents an integer in the range of 1 to 6, and the following general formula (3)
ROH (3)
(Wherein, R is an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group, or. A trialkylsilyl group having 3 to 10 carbon atoms), which comprises reacting a compound and a base represented by The following general formula (4)
Ar- (O-R) m (4)
(In the formula, Ar has the same definition as Ar in the general formula (1), R has the same definition as R in the general formula (3), and m represents an integer in the range of 1 to 3). A method for producing an aromatic ether.
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