CN101445437B - 催化合成二芳基醚的改进的方法 - Google Patents
催化合成二芳基醚的改进的方法 Download PDFInfo
- Publication number
- CN101445437B CN101445437B CN200810178469.9A CN200810178469A CN101445437B CN 101445437 B CN101445437 B CN 101445437B CN 200810178469 A CN200810178469 A CN 200810178469A CN 101445437 B CN101445437 B CN 101445437B
- Authority
- CN
- China
- Prior art keywords
- chemical formula
- reaction
- aryl
- salt
- group
- 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
- 150000001987 diarylethers Chemical class 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims description 19
- 238000007036 catalytic synthesis reaction Methods 0.000 title description 3
- 230000008569 process Effects 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
- -1 heteroaryl bromide Chemical compound 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 8
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 7
- MCMFEZDRQOJKMN-UHFFFAOYSA-N 1-butylimidazole Chemical compound CCCCN1C=CN=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-N 0.000 claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 125000003944 tolyl group Chemical group 0.000 claims description 6
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 229910052728 basic metal Inorganic materials 0.000 claims description 2
- 150000003818 basic metals Chemical class 0.000 claims description 2
- 229910021593 Copper(I) fluoride Inorganic materials 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 6
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 abstract description 5
- 125000003107 substituted aryl group Chemical group 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 28
- 150000002989 phenols Chemical class 0.000 description 19
- 239000010949 copper Substances 0.000 description 14
- 238000010168 coupling process Methods 0.000 description 14
- 238000005859 coupling reaction Methods 0.000 description 13
- 230000008878 coupling Effects 0.000 description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 229910052802 copper Inorganic materials 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 5
- 150000001502 aryl halides Chemical class 0.000 description 5
- 150000001503 aryl iodides Chemical class 0.000 description 5
- 238000006555 catalytic reaction Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 150000001879 copper Chemical class 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000006880 cross-coupling reaction Methods 0.000 description 3
- 230000002950 deficient Effects 0.000 description 3
- JGUQDUKBUKFFRO-CIIODKQPSA-N dimethylglyoxime Chemical compound O/N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-CIIODKQPSA-N 0.000 description 3
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229960003742 phenol Drugs 0.000 description 3
- SCWKRWCUMCMVPW-UHFFFAOYSA-N phenyl n-methylcarbamate Chemical group CNC(=O)OC1=CC=CC=C1 SCWKRWCUMCMVPW-UHFFFAOYSA-N 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 235000015320 potassium carbonate Nutrition 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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
- 238000006887 Ullmann reaction Methods 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 150000004694 iodide salts Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 230000007170 pathology Effects 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000035899 viability Effects 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- KKKDZZRICRFGSD-UHFFFAOYSA-N 1-benzylimidazole Chemical compound C1=CN=CN1CC1=CC=CC=C1 KKKDZZRICRFGSD-UHFFFAOYSA-N 0.000 description 1
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical class C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 1
- KAIPKTYOBMEXRR-UHFFFAOYSA-N 1-butyl-3-methyl-2h-imidazole Chemical compound CCCCN1CN(C)C=C1 KAIPKTYOBMEXRR-UHFFFAOYSA-N 0.000 description 1
- SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical compound C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 description 1
- NHNAEZDWNCRWRW-UHFFFAOYSA-N 2-bromobenzamide Chemical class NC(=O)C1=CC=CC=C1Br NHNAEZDWNCRWRW-UHFFFAOYSA-N 0.000 description 1
- 150000005762 2-bromopyridine Chemical class 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 206010027336 Menstruation delayed Diseases 0.000 description 1
- VIHYIVKEECZGOU-UHFFFAOYSA-N N-acetylimidazole Chemical compound CC(=O)N1C=CN=C1 VIHYIVKEECZGOU-UHFFFAOYSA-N 0.000 description 1
- AGTKZMNBQCCEQY-UHFFFAOYSA-N N-methyl-N-[trihydroxy(methyl)-lambda5-phosphanyl]methanamine Chemical class CN(C)P(C)(O)(O)O AGTKZMNBQCCEQY-UHFFFAOYSA-N 0.000 description 1
- 229910000545 Nickel–aluminium alloy Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229940054066 benzamide antipsychotics Drugs 0.000 description 1
- 150000003936 benzamides Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 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
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- BPLKXBNWXRMHRE-UHFFFAOYSA-N copper;1,10-phenanthroline Chemical compound [Cu].C1=CN=C2C3=NC=CC=C3C=CC2=C1 BPLKXBNWXRMHRE-UHFFFAOYSA-N 0.000 description 1
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- CANPFCFJURGKAX-JTQLQIEISA-N iolopride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=C(O)C(I)=CC=C1OC CANPFCFJURGKAX-JTQLQIEISA-N 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229960001708 magnesium carbonate Drugs 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- ILCQYORZHHFLNL-UHFFFAOYSA-N n-bromoaniline Chemical compound BrNC1=CC=CC=C1 ILCQYORZHHFLNL-UHFFFAOYSA-N 0.000 description 1
- UNDODZOTYQJDEK-UHFFFAOYSA-N n-ethyl-2-(3-methylphenoxy)benzamide Chemical compound CCNC(=O)C1=CC=CC=C1OC1=CC=CC(C)=C1 UNDODZOTYQJDEK-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 229960003418 phenoxybenzamine Drugs 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012041 precatalyst Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- ORIHZIZPTZTNCU-YVMONPNESA-N salicylaldoxime Chemical compound O\N=C/C1=CC=CC=C1O ORIHZIZPTZTNCU-YVMONPNESA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07122010.7 | 2007-11-30 | ||
| EP07122010A EP2065356A1 (en) | 2007-11-30 | 2007-11-30 | Improved process for the catalytic synthesis of diaryl ethers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101445437A CN101445437A (zh) | 2009-06-03 |
| CN101445437B true CN101445437B (zh) | 2014-07-02 |
Family
ID=39311529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200810178469.9A Expired - Fee Related CN101445437B (zh) | 2007-11-30 | 2008-12-01 | 催化合成二芳基醚的改进的方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8304550B2 (enExample) |
| EP (2) | EP2065356A1 (enExample) |
| JP (1) | JP5441395B2 (enExample) |
| CN (1) | CN101445437B (enExample) |
| ES (1) | ES2471451T3 (enExample) |
| PL (1) | PL2065357T3 (enExample) |
| PT (1) | PT2065357E (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011013834A1 (ja) * | 2009-07-31 | 2011-02-03 | 住友化学株式会社 | ビアリール化合物の製造方法 |
| CN102070471A (zh) * | 2011-01-14 | 2011-05-25 | 荆州市丽之源化工科技有限公司 | 医药中间体2-苯氧基苯胺及其制备方法 |
| CN102875273A (zh) * | 2012-05-23 | 2013-01-16 | 温州大学 | 一种杂芳基醚的合成方法 |
| CN103086851B (zh) * | 2013-01-31 | 2015-12-23 | 中国科学院上海有机化学研究所 | 含芴和苯并环丁烯结构单元的热固性树脂单体、制备方法和应用 |
| CN104326947B (zh) * | 2013-10-14 | 2016-08-24 | 大连理工大学 | 活性艳蓝k-gr中间体的制备方法 |
| CN105001029B (zh) * | 2015-05-25 | 2016-08-17 | 常州大学 | 一种光催化二芳基醚衍生物的合成方法 |
| CN105198713B (zh) * | 2015-09-30 | 2017-05-10 | 黄山学院 | 一种利用微波催化合成3，4’‑二氯二苯醚的方法 |
| CN108129277A (zh) * | 2018-01-19 | 2018-06-08 | 上海博栋化学科技有限公司 | 一种合成2,2’-二萘醚的方法 |
| CN108586329A (zh) * | 2018-03-31 | 2018-09-28 | 山东罗欣药业集团恒欣药业有限公司 | 一种索拉非尼的合成方法 |
| CN109824544A (zh) * | 2019-03-11 | 2019-05-31 | 三峡大学 | 新型的eda瞬态电子给受体络合物，制备方法及其应用 |
| CN110982806B (zh) * | 2019-08-30 | 2022-09-02 | 浙江工业大学 | 一种蛋白质芳基衍生物及其制备方法 |
| CN112707801A (zh) * | 2020-12-30 | 2021-04-27 | 锦州三丰科技有限公司 | 一种间苯氧基苯甲醛的制备方法 |
| CN113651705A (zh) * | 2021-08-26 | 2021-11-16 | 襄阳金达成精细化工有限公司 | 一种4-苯氧基-2，6-二异丙基苯胺中间体及其制备方法和应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4404359A (en) * | 1981-07-23 | 1983-09-13 | Basf Aktiengesellschaft | Preparation of polyphenylene ethers |
| CN1684944A (zh) * | 2002-08-02 | 2005-10-19 | 麻省理工学院 | 铜催化形成碳－杂原子和碳－碳键的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55120530A (en) * | 1979-03-09 | 1980-09-17 | Nippon Soda Co Ltd | Preparation of 3-phenoxybenzyl alcohol |
| JPH01160935A (ja) * | 1987-12-16 | 1989-06-23 | Yoshitomi Pharmaceut Ind Ltd | ４−ビフェニルｐ−トリルエーテルの製造法 |
| JPH07107028B2 (ja) * | 1988-04-21 | 1995-11-15 | ダイセル化学工業株式会社 | ２，６−ジエチル−４−フェノキシアリニン誘導体及びその製造法 |
| JPH0791248B2 (ja) * | 1988-06-29 | 1995-10-04 | 富士写真フイルム株式会社 | アルコキシもしくはアリールオキシベンゼン化合物の製造方法 |
| JPH0717890A (ja) * | 1993-06-30 | 1995-01-20 | Sanko Chem Co Ltd | ４−（４−メチルフェニルオキシ）−ビフェニルの製造方法 |
| JPH0971549A (ja) * | 1995-09-06 | 1997-03-18 | Nitto Kasei Co Ltd | ジアリ−ルエ−テル化合物の製造方法 |
-
2007
- 2007-11-30 EP EP07122010A patent/EP2065356A1/en not_active Withdrawn
-
2008
- 2008-11-17 EP EP08169219.6A patent/EP2065357B1/en not_active Not-in-force
- 2008-11-17 PT PT81692196T patent/PT2065357E/pt unknown
- 2008-11-17 PL PL08169219T patent/PL2065357T3/pl unknown
- 2008-11-17 ES ES08169219.6T patent/ES2471451T3/es active Active
- 2008-11-21 US US12/275,316 patent/US8304550B2/en not_active Expired - Fee Related
- 2008-11-21 JP JP2008298711A patent/JP5441395B2/ja not_active Expired - Fee Related
- 2008-12-01 CN CN200810178469.9A patent/CN101445437B/zh not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4404359A (en) * | 1981-07-23 | 1983-09-13 | Basf Aktiengesellschaft | Preparation of polyphenylene ethers |
| CN1684944A (zh) * | 2002-08-02 | 2005-10-19 | 麻省理工学院 | 铜催化形成碳－杂原子和碳－碳键的方法 |
Non-Patent Citations (10)
| Title |
|---|
| Copper in cross-coupling reactions The post-Ullmann chemistry;Irina P.Beletskaya,Andrei V.Cheprakov;《Coordination Chemistry Reviews》;20041231;第248卷;2337-2364 * |
| Copper(I) Chloride Catalyzed Synthesis of Diaryl Ethers in Ionic Liquids Under Mild Conditions;S.M.S.Chauhan,et al.;《Synthetic Communications》;20031231;第33卷(第20期);3607-3614 * |
| Copper(II) and 2,2"-Biimidazolyl-promoted Ullmann Coupling Reaction of Phenols and Aryl Iodides;Wang,Bao-An,et al.;《Chinese Journal of Chemistry》;20061231;第24卷(第8期);1062-1065 * |
| Elena Sperotto,et al..Ligand-free copper(I) catalyzed N- and O-arylation of aryl halides.《Tetrahedron Lett.》.2007,第48卷7366-7370. |
| Irina P.Beletskaya,Andrei V.Cheprakov.Copper in cross-coupling reactions The post-Ullmann chemistry.《Coordination Chemistry Reviews》.2004,第248卷2337-2364. |
| Ligand-free copper(I) catalyzed N- and O-arylation of aryl halides;Elena Sperotto,et al.;《Tetrahedron Lett.》;20070810;第48卷;7366-7370 * |
| S.M.S.Chauhan,et al..Copper(I) Chloride Catalyzed Synthesis of Diaryl Ethers in Ionic Liquids Under Mild Conditions.《Synthetic Communications》.2003,第33卷(第20期),3607-3614. |
| Ullmann Diary Ether Synthesis in Ionic Liquids;Yunting Luo,et al.;《Synlett》;20030825(第11期);1734-1736 * |
| Wang,Bao-An,et al..Copper(II) and 2,2"-Biimidazolyl-promoted Ullmann Coupling Reaction of Phenols and Aryl Iodides.《Chinese Journal of Chemistry》.2006,第24卷(第8期),1062-1065. |
| Yunting Luo,et al..Ullmann Diary Ether Synthesis in Ionic Liquids.《Synlett》.2003,(第11期),1734-1736. |
Also Published As
| Publication number | Publication date |
|---|---|
| PT2065357E (pt) | 2014-06-24 |
| EP2065357A1 (en) | 2009-06-03 |
| PL2065357T3 (pl) | 2014-09-30 |
| EP2065357B1 (en) | 2014-04-23 |
| US20090143594A1 (en) | 2009-06-04 |
| JP2009132713A (ja) | 2009-06-18 |
| EP2065356A1 (en) | 2009-06-03 |
| JP5441395B2 (ja) | 2014-03-12 |
| US8304550B2 (en) | 2012-11-06 |
| ES2471451T3 (es) | 2014-06-26 |
| CN101445437A (zh) | 2009-06-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101445437B (zh) | 催化合成二芳基醚的改进的方法 | |
| Saito et al. | A synthesis of biaryls via nickel (0)-catalyzed cross-coupling reaction of chloroarenes with phenylboronic acids | |
| Castanet et al. | Asymmetric Suzuki cross-coupling reaction: chirality reversal depending on the palladium–chiral phosphine ratio | |
| CN102050687B (zh) | 一种水相体系中以氨水为氨源制备芳香伯胺的方法 | |
| CN105585473B (zh) | 一种制备丙炔酸类化合物的方法 | |
| EP3315486A1 (en) | Method for producing aromatic compound | |
| CN104844399A (zh) | 一种合成2-氟代苯酚化合物的方法 | |
| CN101774874B (zh) | 以吡咯-2-酰肼类化合物为配体的水相体系中的n-芳基化方法 | |
| CN102049301B (zh) | 一种高效离子液体交聚苯乙烯负载钯催化剂及其应用 | |
| Peng et al. | Highly active and reusable copper phthalocyanine derivatives catalyzed the hydroxylation of (hetero) aryl halides | |
| CN109096146B (zh) | 阿那曲唑关键中间体的合成方法 | |
| CN101691318A (zh) | 以取代二酰肼为配体的水相体系中的n-芳基化方法 | |
| CN101143331B (zh) | 一种用于偶联反应的非钯催化剂体系 | |
| CN103254250B (zh) | 二茂铁基吡嗪环钯氮杂环卡宾化合物及其制备方法和用途 | |
| CN111138259B (zh) | 一种制备二芳基醚化合物的方法 | |
| CN114832862B (zh) | 一种偶联反应的催化组合物及其在制备异喹啉-1，3-二酮类化合物中的应用 | |
| CN103254065B (zh) | 2,4,4＇,6-四羧酸联苯银配合物及其制备方法和用途 | |
| CN102060790B (zh) | 一种喹喔啉双n-氧化物衍生物配体及其在促进铜催化c-o偶联反应的应用 | |
| JPH0429957A (ja) | ビアリール誘導体の製造方法 | |
| CN104610002B (zh) | 一种芳香肼合成对称性联苯的方法 | |
| CN109704987B (zh) | 一种合成2-氟苯胺化合物的方法 | |
| Liu et al. | hindered substrates in pure water | |
| CN101445518B (zh) | 膦配体的制备方法 | |
| CN120736991A (zh) | 一种α-支化胺衍生物的水相制备方法 | |
| CN105777538B (zh) | 一种医药中间体苄基酯类化合物的合成方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20140702 Termination date: 20161201 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |