2-Bromo-4-trifluoromethylaniline → 4-Amino-3-cyanobenzotrifluoride

HRID 131327

反応式

HRID 131327 の反応式
[Cu][C:2]#[N:3].Br[C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:6]=1[NH2:15]>CN1CCCC1=O.C(OCC)(=O)C>[NH2:15][C:6]1[CH:5]=[CH:10][C:9]([C:11]([F:12])([F:13])[F:14])=[CH:8][C:7]=1[C:2]#[N:3]

参加物

5

反応物 2

HCID 938992-Bromo-4-trifluoromethylanilineHCID 178418546HCID 178418546、化合物

生成物 1

HCID 126273614-Amino-3-cyanobenzotrifluoride収率 47%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

Heat a mixture of copper (I) cyanide (2.24 g, 25.00 mmol) and 2-bromo-4-trifluoromethyl-phenylamine (5.0 g, 20.83 mmol from Avocado) in 1-methyl-2-pyrrolidinone (20 ml) to 195° C. for four hours. Dilute the reaction mixture with 100 ml of ethyl acetate and wash the dark solution twice with 28% aqueous ammonium hydroxide, twice with saturated aqueous sodium chloride (brine) and twice with water. Collect the organic layer, dry over sodium sulfate and remove the solvent under reduced pressure. Purify the residue via flash chromatography eluting with a step gradient starting with hexanes and going to 70% hexanes with 30% ethyl acetate to obtain 1.821 g (9.78 mmol, 47% yield) the title compound as a green amorphous solid: Mass Spectrum (m/e): 187(M+1).

後処理

  1. temperatureHeat
  2. washwash the dark solution twice with 28% aqueous ammonium hydroxide
  3. customCollect the organic layer
  4. dry with materialdry over sodium sulfate
  5. customremove the solvent under reduced pressure
  6. customPurify the residue via flash chromatography
  7. washeluting with a step gradient

出典と根拠

ORDレコード
ord-4be442a3741e4283909eab11721f7e9a
出典データセット
uspto-grants-2008_06
特許番号
US07384934B2

関連ノート

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