DE2435098C3 - Verfahren zur Herstellung von ß- Bromalkyl- und ß-Bromalkenylsulfonen - Google Patents
Verfahren zur Herstellung von ß- Bromalkyl- und ß-BromalkenylsulfonenInfo
- Publication number
- DE2435098C3 DE2435098C3 DE2435098A DE2435098A DE2435098C3 DE 2435098 C3 DE2435098 C3 DE 2435098C3 DE 2435098 A DE2435098 A DE 2435098A DE 2435098 A DE2435098 A DE 2435098A DE 2435098 C3 DE2435098 C3 DE 2435098C3
- Authority
- DE
- Germany
- Prior art keywords
- mmol
- mixture
- bromo
- reaction
- chloride
- 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
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000003457 sulfones Chemical class 0.000 title claims 2
- -1 Sulfonic acid bromides Chemical class 0.000 claims description 45
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 16
- 150000001336 alkenes Chemical class 0.000 claims description 15
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 claims description 15
- 238000007269 dehydrobromination reaction Methods 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 238000007259 addition reaction Methods 0.000 claims description 6
- 150000002432 hydroperoxides Chemical class 0.000 claims description 6
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 229910052738 indium Inorganic materials 0.000 claims description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052716 thallium Inorganic materials 0.000 claims description 2
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 46
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 36
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 28
- 239000011592 zinc chloride Substances 0.000 description 23
- 235000005074 zinc chloride Nutrition 0.000 description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- ARGCQEVBJHPOGB-UHFFFAOYSA-N 2,5-dihydrofuran Chemical compound C1OCC=C1 ARGCQEVBJHPOGB-UHFFFAOYSA-N 0.000 description 16
- 238000009835 boiling Methods 0.000 description 12
- ITYJDNHFRZSTJY-UHFFFAOYSA-N methanesulfonyl bromide Chemical compound CS(Br)(=O)=O ITYJDNHFRZSTJY-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 6
- CGWWQPZGKPHLBU-UHFFFAOYSA-N benzenesulfonyl bromide Chemical compound BrS(=O)(=O)C1=CC=CC=C1 CGWWQPZGKPHLBU-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- YNVXNDHKPUZGRN-UHFFFAOYSA-N (4-methylcyclohexen-1-yl)sulfonylbenzene Chemical compound C1C(C)CCC(S(=O)(=O)C=2C=CC=CC=2)=C1 YNVXNDHKPUZGRN-UHFFFAOYSA-N 0.000 description 4
- ZDTXCVNRZAWLNS-UHFFFAOYSA-N 3-bromo-4-methylsulfonyloxolane Chemical compound CS(=O)(=O)C1COCC1Br ZDTXCVNRZAWLNS-UHFFFAOYSA-N 0.000 description 4
- UIIKOHJPLVXVNT-UHFFFAOYSA-N COCC(C(S(C)(=O)=O)=COC)Br Chemical compound COCC(C(S(C)(=O)=O)=COC)Br UIIKOHJPLVXVNT-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- YOUYRGPEJNZDAY-UHFFFAOYSA-N 2-bromo-1,4-dimethoxy-3-methylsulfonylbutane Chemical compound COCC(Br)C(S(C)(=O)=O)COC YOUYRGPEJNZDAY-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- YBRAOJRURQGUAD-UHFFFAOYSA-N (1-bromo-2-methylsulfonylethyl)benzene Chemical compound CS(=O)(=O)CC(Br)C1=CC=CC=C1 YBRAOJRURQGUAD-UHFFFAOYSA-N 0.000 description 2
- ATPWLKDQBMDRPB-UHFFFAOYSA-N (2-bromocyclohexyl)sulfonylbenzene Chemical compound BrC1CCCCC1S(=O)(=O)C1=CC=CC=C1 ATPWLKDQBMDRPB-UHFFFAOYSA-N 0.000 description 2
- PYBPHLWUZVUNJV-UHFFFAOYSA-N 1,4-dimethoxy-2-methylsulfonylbut-1-ene Chemical compound CS(=O)(=O)C(=COC)CCOC PYBPHLWUZVUNJV-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- KLAQJELBCOXDSM-UHFFFAOYSA-N 1-bromo-2-methylsulfonylcyclopentane Chemical compound CS(=O)(=O)C1CCCC1Br KLAQJELBCOXDSM-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 2
- BMNYWUGACPCXEX-UHFFFAOYSA-N 2-(benzenesulfonyl)-3-bromobicyclo[2.2.1]heptane Chemical compound BrC1C(C2)CCC2C1S(=O)(=O)C1=CC=CC=C1 BMNYWUGACPCXEX-UHFFFAOYSA-N 0.000 description 2
- VUXUTVQVORATFC-UHFFFAOYSA-N 3-bromo-4-(4-nitrophenyl)sulfonyloxolane Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)C1C(Br)COC1 VUXUTVQVORATFC-UHFFFAOYSA-N 0.000 description 2
- WYWOOCCJDYNXJH-UHFFFAOYSA-N 3-bromo-4-ethylsulfonyloxolane Chemical compound CCS(=O)(=O)C1COCC1Br WYWOOCCJDYNXJH-UHFFFAOYSA-N 0.000 description 2
- FSWCCQWDVGZMRD-UHFFFAOYSA-N 4-methylcyclohexene Chemical compound CC1CCC=CC1 FSWCCQWDVGZMRD-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- JFYVDTXNJUUMRN-UHFFFAOYSA-N ac1lgxp2 Chemical compound C1=CC(C(OC(=O)C)=CS2)=C3C2=CC=CC3=C1 JFYVDTXNJUUMRN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 2
- ZKWWAROSTBDFDD-UHFFFAOYSA-N benzenesulfonic acid;hydrobromide Chemical compound Br.OS(=O)(=O)C1=CC=CC=C1 ZKWWAROSTBDFDD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KWYMVQMYZBVTAZ-UHFFFAOYSA-N butane-1-sulfonyl bromide Chemical compound CCCCS(Br)(=O)=O KWYMVQMYZBVTAZ-UHFFFAOYSA-N 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- KPWJBEFBFLRCLH-UHFFFAOYSA-L cadmium bromide Chemical compound Br[Cd]Br KPWJBEFBFLRCLH-UHFFFAOYSA-L 0.000 description 2
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 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
- 238000004821 distillation Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- MCVVUJPXSBQTRZ-ONEGZZNKSA-N methyl (e)-but-2-enoate Chemical compound COC(=O)\C=C\C MCVVUJPXSBQTRZ-ONEGZZNKSA-N 0.000 description 2
- LYHAFGXRDMZEGW-UHFFFAOYSA-N methyl 2-bromo-3-methylsulfonylbutanoate Chemical compound COC(=O)C(Br)C(C)S(C)(=O)=O LYHAFGXRDMZEGW-UHFFFAOYSA-N 0.000 description 2
- 230000036651 mood Effects 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- UHEPJGULSIKKTP-UHFFFAOYSA-N sulcatone Chemical compound CC(C)=CCCC(C)=O UHEPJGULSIKKTP-UHFFFAOYSA-N 0.000 description 2
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- XGXHQTOJAPGZNO-UHFFFAOYSA-N (1-bromo-1-ethoxy-2-methylpropan-2-yl)sulfonylbenzene Chemical compound CCOC(Br)C(C)(C)S(=O)(=O)C1=CC=CC=C1 XGXHQTOJAPGZNO-UHFFFAOYSA-N 0.000 description 1
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- YHHHHJCAVQSFMJ-FNORWQNLSA-N (3e)-deca-1,3-diene Chemical compound CCCCCC\C=C\C=C YHHHHJCAVQSFMJ-FNORWQNLSA-N 0.000 description 1
- RBCOYOYDYNXAFA-UHFFFAOYSA-L (5-hydroxy-4,6-dimethylpyridin-3-yl)methyl phosphate Chemical compound CC1=NC=C(COP([O-])([O-])=O)C(C)=C1O RBCOYOYDYNXAFA-UHFFFAOYSA-L 0.000 description 1
- HXZKBZWDVZHOPR-UHFFFAOYSA-N (5-methylcyclohexen-1-yl)sulfonylbenzene Chemical compound C1C(C)CCC=C1S(=O)(=O)C1=CC=CC=C1 HXZKBZWDVZHOPR-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- FPXUGGUFKHOGBY-HWKANZROSA-N (E)-1,4-dimethoxybut-1-ene Chemical compound COCC\C=C\OC FPXUGGUFKHOGBY-HWKANZROSA-N 0.000 description 1
- VOPRTKOOBAUJAM-UHFFFAOYSA-N 1,1-dichloro-2-(2,2-dichloroethylsulfonyl)ethane Chemical compound ClC(Cl)CS(=O)(=O)CC(Cl)Cl VOPRTKOOBAUJAM-UHFFFAOYSA-N 0.000 description 1
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical group ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- QTYUSOHYEPOHLV-FNORWQNLSA-N 1,3-Octadiene Chemical compound CCCC\C=C\C=C QTYUSOHYEPOHLV-FNORWQNLSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UOXYNCDQUYPYRY-UHFFFAOYSA-N 1-bromo-2-methylsulfonylcyclohexane Chemical compound CS(=O)(=O)C1CCCCC1Br UOXYNCDQUYPYRY-UHFFFAOYSA-N 0.000 description 1
- KTNXZNRAHFETOD-UHFFFAOYSA-N 1-butylsulfonylcyclohexene Chemical compound CCCCS(=O)(=O)C1=CCCCC1 KTNXZNRAHFETOD-UHFFFAOYSA-N 0.000 description 1
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- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
- SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2435098A DE2435098C3 (de) | 1974-07-22 | 1974-07-22 | Verfahren zur Herstellung von ß- Bromalkyl- und ß-Bromalkenylsulfonen |
| CA231,424A CA1076593A (en) | 1974-07-22 | 1975-07-11 | MANUFACTURE OF .beta.-BROMOALKYLSULFONES AND .beta.-BROMOALKENYLSULFONES |
| US05/596,305 US4022804A (en) | 1974-07-22 | 1975-07-16 | Process for the production of bromo substituted tetrahydrofuran sulfones |
| NL7508585A NL7508585A (nl) | 1974-07-22 | 1975-07-17 | Werkwijze voor het bereiden van (beta)-broomalkyl- en (beta)-broomalkenylsulfonen. |
| CH940275A CH612419A5 (enExample) | 1974-07-22 | 1975-07-17 | |
| JP50087429A JPS5912115B2 (ja) | 1974-07-22 | 1975-07-18 | β−ブロムアルキル−及びβ−ブロムアルケニルスルホンの製法 |
| FR7522685A FR2279727A1 (fr) | 1974-07-22 | 1975-07-21 | Procede de preparation de beta-bromalcoyl- et de beta-bromalcenylsulfones |
| AT561275A AT340375B (de) | 1974-07-22 | 1975-07-21 | Verfahren zur herstellung von beta-bromalkyl- und beta-bromalkenylsulfonen |
| HU75BA00003306A HU171405B (hu) | 1974-07-22 | 1975-07-21 | Sposob poluchenija beta-bromalkil- i beta-bromalkenil-sul'fonov |
| GB30379/75A GB1505922A (en) | 1974-07-22 | 1975-07-21 | Manufacture of beta-bromoalkylsulphones and beta-bromoalkenylsulphones |
| BE158490A BE831597A (fr) | 1974-07-22 | 1975-07-22 | Procede de preparation de beta-bromalcoyl- et de beta-bromalcenyl-sulfones |
| YU01862/75A YU186275A (en) | 1974-07-22 | 1975-07-22 | Process for obtaining bromotetrahydrofuran |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2435098A DE2435098C3 (de) | 1974-07-22 | 1974-07-22 | Verfahren zur Herstellung von ß- Bromalkyl- und ß-Bromalkenylsulfonen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2435098A1 DE2435098A1 (de) | 1976-02-12 |
| DE2435098B2 DE2435098B2 (de) | 1977-12-15 |
| DE2435098C3 true DE2435098C3 (de) | 1978-08-10 |
Family
ID=5921146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2435098A Expired DE2435098C3 (de) | 1974-07-22 | 1974-07-22 | Verfahren zur Herstellung von ß- Bromalkyl- und ß-Bromalkenylsulfonen |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4022804A (enExample) |
| JP (1) | JPS5912115B2 (enExample) |
| AT (1) | AT340375B (enExample) |
| BE (1) | BE831597A (enExample) |
| CA (1) | CA1076593A (enExample) |
| CH (1) | CH612419A5 (enExample) |
| DE (1) | DE2435098C3 (enExample) |
| FR (1) | FR2279727A1 (enExample) |
| GB (1) | GB1505922A (enExample) |
| HU (1) | HU171405B (enExample) |
| NL (1) | NL7508585A (enExample) |
| YU (1) | YU186275A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2935682A1 (de) * | 1979-09-04 | 1981-03-12 | Bayer Ag, 5090 Leverkusen | Carbonsaeurederivate. |
| US4604480A (en) * | 1983-08-15 | 1986-08-05 | The Research Foundation Of State University Of New York | Method for the preparation of sulfones and compounds containing carbon chains having conjugated unsaturation and the compounds resulting from such method |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2573580A (en) * | 1949-03-23 | 1951-10-30 | Us Rubber Co | Preparation of aromatic sulfones |
-
1974
- 1974-07-22 DE DE2435098A patent/DE2435098C3/de not_active Expired
-
1975
- 1975-07-11 CA CA231,424A patent/CA1076593A/en not_active Expired
- 1975-07-16 US US05/596,305 patent/US4022804A/en not_active Expired - Lifetime
- 1975-07-17 CH CH940275A patent/CH612419A5/xx not_active IP Right Cessation
- 1975-07-17 NL NL7508585A patent/NL7508585A/xx not_active Application Discontinuation
- 1975-07-18 JP JP50087429A patent/JPS5912115B2/ja not_active Expired
- 1975-07-21 AT AT561275A patent/AT340375B/de active
- 1975-07-21 GB GB30379/75A patent/GB1505922A/en not_active Expired
- 1975-07-21 FR FR7522685A patent/FR2279727A1/fr active Granted
- 1975-07-21 HU HU75BA00003306A patent/HU171405B/hu unknown
- 1975-07-22 BE BE158490A patent/BE831597A/xx not_active IP Right Cessation
- 1975-07-22 YU YU01862/75A patent/YU186275A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2435098A1 (de) | 1976-02-12 |
| CA1076593A (en) | 1980-04-29 |
| HU171405B (hu) | 1978-01-28 |
| FR2279727A1 (fr) | 1976-02-20 |
| DE2435098B2 (de) | 1977-12-15 |
| NL7508585A (nl) | 1976-01-26 |
| GB1505922A (en) | 1978-04-05 |
| BE831597A (fr) | 1976-01-22 |
| ATA561275A (de) | 1977-04-15 |
| CH612419A5 (enExample) | 1979-07-31 |
| FR2279727B1 (enExample) | 1980-04-30 |
| YU186275A (en) | 1982-02-28 |
| JPS5912115B2 (ja) | 1984-03-21 |
| JPS5136421A (en) | 1976-03-27 |
| US4022804A (en) | 1977-05-10 |
| AT340375B (de) | 1977-12-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8330 | Complete disclaimer |