Carbon Dioxide → HCID 66957735, 화합물

HRID 2063194

반응식

HRID 2063194 반응식
C([Li])CCC.[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[C:8]=1[S:17][CH3:18].[C:19](=[O:21])=[O:20].O>O1CCCC1.C(OCC)C>[F:6][C:7]1[C:8]([S:17][CH3:18])=[C:9]([C:13]([F:15])([F:16])[F:14])[CH:10]=[CH:11][C:12]=1[C:19]([OH:21])=[O:20]

참가 물질

7

반응물 4

HCID 280Carbon DioxideHCID 962WaterHCID 4145933Benzene, 1-fluoro-2-(methylthio)-3-(trifluoromethyl)-HCID 178418339Butyllithium

생성물 1

HCID 66957735HCID 66957735, 화합물

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

Under an atmosphere of inert gas, 27.5 ml (1.6 M in hexane, 44 mmol) of n-butyllithium were added dropwise to a solution, cooled to −78° C., of 7.98 g (38 mmol) of 1-fluoro-2-methylthio-3-(trifluoromethyl)benzene in 60 ml of anhydrous tetrahydrofuran, where the temperature of the reaction mixture should not exceed −65° C. The mixture was stirred at −78° C. for 3 h, and at this temperature a carbon dioxide stream was then introduced such that the temperature of the reaction mixture did not exceed −45° C. The mixture was then warmed to RT and then once more cooled to 0° C. For work-up, water was added dropwise at this temperature until the precipitate formed had dissolved. Diethyl ether was added, and the organic phase was extracted three times with water. The combined aqueous phases were acidified with 10 percent strength hydrochloric acid. The aqueous phase was extracted repeatedly with dichloromethane, the combined organic phases were washed with saturated aqueous NaCl solution and dried over sodium sulfate and the filtrate was finally freed from the solvent. The crude product obtained in this manner was recrystallized from gasoline/ethyl acetate. This gave 6.8 g of 2-fluoro-3-methylthio-4-(trifluoromethyl)benzoic acid.

후처리

  1. customexceed −65° C
  2. customdid not exceed −45° C
  3. temperatureThe mixture was then warmed to RT
  4. temperatureonce more cooled to 0° C
  5. customformed
  6. dissolutionhad dissolved
  7. extractionthe organic phase was extracted three times with water
  8. extractionThe aqueous phase was extracted repeatedly with dichloromethane
  9. washthe combined organic phases were washed with saturated aqueous NaCl solution
  10. dry with materialdried over sodium sulfate

출처 및 근거

ORD 기록
ord-86b16303c40d4454bd7c7a53267e9871
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288319B2

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