Sodium Cyanide → 5-Bromo-4-methylpyridine-2-carbonitrile

HRID 1047229

反応式

HRID 1047229 の反応式
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:9])=[CH:4][N:3]=1.[Cu](C#N)[C:11]#[N:12].[C-]#N.[Na+]>CN(C)C=O>[Br:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([C:11]#[N:12])=[N:3][CH:4]=1

参加物

5

反応物 3

HCID 8929Sodium CyanideHCID 27344292,5-Dibromo-4-methylpyridineHCID 178418260HCID 178418260、化合物

生成物 1

HCID 533954685-Bromo-4-methylpyridine-2-carbonitrile収率 73%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
158 °C

実験手順

2,5-Dibromo-4-methylpyridine (5.0 g, 19.9 mmol), copper cyanide (1.43 g, 15.9 mmol), sodium cyanide (0.801 g, 16.3 mmol) and dimethylformamide (30 mL) were combined in a sealed reaction vessel and heated at 158° C. for 3 h. The reaction mixture was purified by silica gel column chromatography (0-80% ethyl acetate in hexanes). The resulting material was subjected to a second silica gel column (0-20% methanol in dichloromethane). Clean fractions were combined and concentrated to afford the title compound as a white solid (2.30 g, 11.6 mmol, 58% yield). MS (ESI) m/z 198.0 [M+1]+.

後処理

  1. customThe reaction mixture was purified by silica gel column chromatography (0-80% ethyl acetate in hexanes)
  2. concentrationconcentrated

出典と根拠

ORDレコード
ord-7189f46228d94371aad57718a868976f
出典データセット
uspto-grants-2013_10
特許番号
US08569494B2

関連ノート

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