Dimethylformamide → 3-Amino-5-(trifluoromethyl)benzonitrile

HRID 517714ノート

反応式

HRID 517714 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5].[CH3:13][N:14](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:5][C:4]1[CH:3]=[C:2]([CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=1)[C:13]#[N:14]

参加物

5

反応物 2

HCID 6228DimethylformamideHCID 27358803-Bromo-5-(trifluoromethyl)aniline

生成物 1

HCID 225022643-Amino-5-(trifluoromethyl)benzonitrile

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
80 °C

実験手順

A solution of 3-bromo-5-(trifluoromethyl)aniline (3.24 g, 13.5 mmol) in N,N-dimethylformamide (50 mL) was degassed by bubbling argon through the solution for 30 minutes. To the reaction was added zinc cyanide (0.872 g, 7.42 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.624 g, 0.54 mmol). The reaction was heated to 80° C. and stirred for 20 hours. The solvent was removed from the reaction under vacuum and the residue purified by silica chromatography (Biotage SP4, eluting 15% EtOAc in iso-hexane (4 column volumes) then a gradient from 15-30% (over 6 column volumes)) to yield the title compound as a colourless oil (2.20 g).

後処理

  1. customby bubbling argon through the solution for 30 minutes
  2. customThe solvent was removed from the reaction under vacuum
  3. customthe residue purified by silica chromatography (Biotage SP4
  4. washeluting 15% EtOAc in iso-hexane (4 column volumes)

出典と根拠

ORDレコード
ord-c74da81e91324318b91d60ec84ef4017
出典データセット
uspto-grants-2015_08
特許番号
US09115132B2

反応ノート

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