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

HRID 425289ノート

反応式

HRID 425289 の反応式
[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

参加物

6

反応物 4

HCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 24758Sodium hydride2 回HCID 7360294-Bromo-2-fluorobenzonitrile

生成物 1

HCID 577253024-Bromo-2-(phenylsulfanyl)benzonitrile収率 96.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ec33a9391ca24958b9817d64a2509aa7
出典データセット
uspto-grants-2012_01
特許番号
US08106207B2

反応ノート

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