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

HRID 517714노트

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HRID 517714 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

HCID 225022643-Amino-5-(trifluoromethyl)benzonitrile

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매

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온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c74da81e91324318b91d60ec84ef4017
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115132B2

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