Thiophenol → 4-Bromo-2-(phenylsulfanyl)benzonitrile

HRID 425289노트

반응식

HRID 425289 반응식
[H-].[Na+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13](F)[CH:12]=1.[OH-].[Na+]>CN(C=O)C>[Br:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([S:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:12]=1

참가 물질

6

반응물 4

HCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 24758Sodium hydride2회HCID 7360294-Bromo-2-fluorobenzonitrile

생성물 1

HCID 577253024-Bromo-2-(phenylsulfanyl)benzonitrile수율 96.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Sodium hydride (2.40 g, 60 mmol) (60% by wt) was weighed into a flask and washed with several hexane rinsings. The hexanes were decanted and discarded and 20 mL DMF was added to the flask. A DMF-solution of benzenethiol (5.1 mL, 50 mmol in 50 mL DMF) was added dropwise to the NaH mixture and stirred at room temperature. To 4-bromo-2-fluoro-benzonitrile (10.0 g, 50 mmol) in 40 mL DMF) was added benzenethiophenoxide (described above), dropwise, over 30 minutes. Upon complete addition, the reaction was stirred at room temperature for 20 min. At that time, the mixture was poured into cold 1 N NaOH. A precipitate formed and was collected by vacuum filtration to give 14.0 g (48.4 mmol) of Compound 1h.

후처리

  1. washwashed with several hexane rinsings
  2. customThe hexanes were decanted
  3. addition20 mL DMF was added to the flask
  4. additionUpon complete addition
  5. stirringthe reaction was stirred at room temperature for 20 min
  6. customA precipitate formed
  7. filtrationwas collected by vacuum filtration

출처 및 근거

ORD 기록
ord-ec33a9391ca24958b9817d64a2509aa7
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106207B2

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