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

HRID 1013940ノート

反応式

HRID 1013940 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-b417c2a775964e92be31a3ef95e1aeef
出典データセット
uspto-grants-2011_07
特許番号
US07982042B2

反応ノート

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