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Water → 4-(2-Bromophenyl)butanenitrile

HRID 1866808
ノート
印刷プレビュー

反応式

HRID 1866808 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10]OS(C)(=O)=O.[C-:16]#[N:17].[K+].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][C:16]#[N:17]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 9032Potassium CyanideHCID 153648793-(2-Bromophenyl)propyl methanesulfonate

生成物 1

HCID 534345084-(2-Bromophenyl)butanenitrile収率 91.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
60 °C

実験手順

Methanesulfonyl chloride (7.7 mL, 97 mmol) in 100 mL dry THF is added to a solution of 3-(2-bromo-phenyl)-propan-1-ol (17.4 g, 80.9 mmol) and triethyl amine (14.7 g, 146 mmol) in 200 mL dry THF at 0° C. under an argon atmosphere. Water is added and the mixture is extracted with ethyl acetate. The organic phase is washed with brine, dried with MgSO4 and concentrated in vacuo to give 23 g (97%) methanesulfonic acid 3-(2-bromo-phenyl)-propyl ester as an oil. Methanesulfonic acid 3-(2-bromo-phenyl)-propyl ester (23 g, 78 mmol) in 300 mL dry DMF is added to a suspension of potassium cyanide (15.3 g, 235 mmol) in dry DMF. The reaction mixture is stirred at 60° C. for 16 hours. Water is added and the mixture is extracted with ethyl acetate (3 times). The organic phase is washed with brine (twice), dried with MgSO4 and concentrated in vacuo. The residue is placed on a plug of silica gel and eluted with ethyl acetate/heptane (1:4) and concentrated in vacuo to give 16.0 g 4-(2-bromo-phenyl)-butyronitrile (91%) as an oil. 300 mL concentrated HCl is added to 4-(2-bromo-phenyl)-butyronitrile (16.0 g, 71 mmol) in 150 mL acetic acid. The reaction mixture is stirred at 60° C. for 16 hours. The reaction mixture concentrated in vacuo partly and is poured into water. The mixture is extracted with ethyl acetate (3 times). The organic phase is washed with brine (twice), dried with MgSO4 and concentrated in vacuo to give the title compound as a crystalline material.

後処理

  1. extractionthe mixture is extracted with ethyl acetate (3 times)
  2. washThe organic phase is washed with brine (twice),
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated in vacuo
  5. washeluted with ethyl acetate/heptane (1:4)
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a6f94fa213cf4ae5a002ff92ed5e6c1e
出典データセット
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07629473B2

反応ノート

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