2-Fluoro-4-(4-trifluoromethylphenyl)benzonitrile → 2-Methylthio-4-(4-trifluoromethylphenyl)benzonitrile

HRID 1432756노트

반응식

HRID 1432756 반응식
F[C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:20][SH:21].[Na]>CN(C)C=O>[CH3:20][S:21][C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

참가 물질

4

반응물 2

HCID 221709242-Fluoro-4-(4-trifluoromethylphenyl)benzonitrileHCID 45051789Methylmercaptan sodium

생성물 1

HCID 221709222-Methylthio-4-(4-trifluoromethylphenyl)benzonitrile수율 75.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To 3.0 g (11.3 mmol) of 2-fluoro-4-(4-trifluoromethylphenyl)benzonitrile in 50 ml of N,N-dimethylformamide, 7.0 g (15.0 mmol) of 15% aqueous sodium methyl mercaptan was added dropwise at room temperature. After 6 hours of stirring at 60° C., the reaction mixture was poured into 200 ml of ice-cold water and extracted with 100 ml of ethyl acetate twice. The ethyl acetate layer was washed with 100 ml of water twice and dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 2.5 g of 2-methylthio-4-(4-trifluoromethylphenyl)benzonitrile (yield 75%) as white crystals (m.p. 128-129° C.).

후처리

  1. extractionextracted with 100 ml of ethyl acetate twice
  2. washThe ethyl acetate layer was washed with 100 ml of water twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe ethyl acetate was distilled off under reduced pressure
  5. customPurification of the residue by silica gel column chromatography

출처 및 근거

ORD 기록
ord-0723a54b94494a068cc023b57e7633d8
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612105B2

반응 노트

불러오는 중…