JPS6136743B2 - - Google Patents

Info

Publication number

JPS6136743B2

JPS6136743B2 JP16013580A JP16013580A JPS6136743B2 JP S6136743 B2 JPS6136743 B2 JP S6136743B2 JP 16013580 A JP16013580 A JP 16013580A JP 16013580 A JP16013580 A JP 16013580A JP S6136743 B2 JPS6136743 B2 JP S6136743B2

Authority

JP

Japan

Prior art keywords

reaction

general formula

ketone

fluoro

represented

Prior art date

1980-11-13

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

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• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
• 150000002148 esters Chemical class 0.000 claims description 10
• 239000002904 solvent Substances 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 238000003797 solvolysis reaction Methods 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 125000000217 alkyl group Chemical group 0.000 claims description 2
• 229910052801 chlorine Inorganic materials 0.000 claims description 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
• 150000002576 ketones Chemical class 0.000 description 13
• -1 fluoromethylene groups Chemical group 0.000 description 11
• 238000000034 method Methods 0.000 description 11
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• 238000006243 chemical reaction Methods 0.000 description 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 238000005796 dehydrofluorination reaction Methods 0.000 description 5
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
• 150000007514 bases Chemical class 0.000 description 4
• QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
• 239000007818 Grignard reagent Substances 0.000 description 3
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
• 150000004795 grignard reagents Chemical class 0.000 description 3
• HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 3
• OBDFQUSHNJZDSN-UHFFFAOYSA-N n-ethylethanamine;1,1,2,3,3,3-hexafluoroprop-1-ene Chemical compound CCNCC.FC(F)=C(F)C(F)(F)F OBDFQUSHNJZDSN-UHFFFAOYSA-N 0.000 description 3
• 239000002994 raw material Substances 0.000 description 3
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• 150000004703 alkoxides Chemical class 0.000 description 2
• 150000001875 compounds Chemical class 0.000 description 2
• 238000007796 conventional method Methods 0.000 description 2
• 238000004821 distillation Methods 0.000 description 2
• 239000007789 gas Substances 0.000 description 2
• 238000010992 reflux Methods 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• 238000005406 washing Methods 0.000 description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• 239000003905 agrochemical Substances 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 150000001499 aryl bromides Chemical class 0.000 description 1
• 125000005840 aryl keto group Chemical group 0.000 description 1
• 125000004429 atom Chemical group 0.000 description 1
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
• 244000309464 bull Species 0.000 description 1
• 235000011089 carbon dioxide Nutrition 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• VCYZVXRKYPKDQB-UHFFFAOYSA-N ethyl 2-fluoroacetate Chemical compound CCOC(=O)CF VCYZVXRKYPKDQB-UHFFFAOYSA-N 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 229910052757 nitrogen Inorganic materials 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• 150000004812 organic fluorine compounds Chemical class 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 150000002905 orthoesters Chemical class 0.000 description 1
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 239000012312 sodium hydride Substances 0.000 description 1
• 229910000104 sodium hydride Inorganic materials 0.000 description 1
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
• 239000000243 solution Substances 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 230000002194 synthesizing effect Effects 0.000 description 1
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1