Benzene, 1-iodo-3-(trifluoromethyl)- → 2,2-Difluoro-1-[3-(trifluoromethyl)phenyl]-1-propanone

HRID 2371079

반응식

HRID 2371079 반응식
CC([Mg]Cl)C.I[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1.[F:17][C:18]([F:26])([CH3:25])[C:19](N(OC)C)=[O:20]>C1COCC1>[F:17][C:18]([F:26])([CH3:25])[C:19]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)=[O:20]

참가 물질

5

반응물 3

HCID 67868Benzene, 1-iodo-3-(trifluoromethyl)-HCID 587363132,2-difluoro-N-methoxy-N-methylpropanamideHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 582479962,2-Difluoro-1-[3-(trifluoromethyl)phenyl]-1-propanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-15 °C

실험 절차

A solution of 2-propylmagnesium chloride in THF (1.3 M, 7.5 ml) was cooled to −15° C. and admixed with 1-iodo-3-(trifluoromethyl)benzene (2.80 g, 10.2 mmol). The reaction mixture was stirred at −15° C. for 1 h, warmed to room temperature and admixed dropwise with a solution of 2,2-difluoro-N-methoxy-N-methylpropanamide (1.43 g, 9.35 mmol: prepared according to Synth. Comm. 2008 (38), 1940-1945), and stirred at room temperature overnight. Then the mixture was added to ice-cold dilute hydrochloric acid and extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by means of silica gel chromatography with the eluent cyclohexane/ethyl acetate (EA) (0% FA to 30% EA).

후처리

  1. temperaturewarmed to room temperature
  2. stirringstirred at room temperature overnight
  3. additionThen the mixture was added to ice-cold dilute hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by means of silica gel chromatography with the eluent cyclohexane/ethyl acetate (EA) (0% FA to 30% EA)

출처 및 근거

ORD 기록
ord-74d2ad7d73b6436c9d6cb8c5a19ab26e
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08710242B2

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