Diphosgene → 1-Bromo-4-isocyanato-2-(trifluoromethyl)benzene

HRID 78325

反応式

HRID 78325 の反応式
Cl.[Br:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][C:4]=1[C:10]([F:13])([F:12])[F:11].Cl[C:15](OC(Cl)(Cl)Cl)=[O:16]>C1(C)C=CC=CC=1>[Br:2][C:3]1[CH:9]=[CH:8][C:6]([N:7]=[C:15]=[O:16])=[CH:5][C:4]=1[C:10]([F:11])([F:12])[F:13]

参加物

4

反応物 2

HCID 10426DiphosgeneHCID 667457074-bromo-3-(trifluoromethyl)aniline HCl salt

生成物 1

HCID 231372171-Bromo-4-isocyanato-2-(trifluoromethyl)benzene収率 86%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A suspension of 4-bromo-3-(trifluoromethyl)aniline HCl salt (36.8 g, 133 mmol) in toluene (278 mL) was treated with trichloromethyl chloroformate dropwise and the resulting mixture was heated at the reflux temp. for 18 h. The resulting mixture was concentrated under reduced pressure. The residue was treated with toluene (500 mL), then concentrated under reduced pressure. The residue was treated with CH2Cl2 (500 mL), then concentrated under reduced pressure. The CH2Cl2 treatment/concentration protocol was repeated and resulting amber oil was stored at −20° C. for 16 h, to afford 4-bromo-3-(trifluoromethyl)phenyl isocyanate as a tan solid (35.1 g, 86%): GC-MS m/z 265 (M+).

後処理

  1. temperaturethe resulting mixture was heated at the reflux temp
  2. concentrationThe resulting mixture was concentrated under reduced pressure
  3. additionThe residue was treated with toluene (500 mL)
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was treated with CH2Cl2 (500 mL)
  6. concentrationconcentrated under reduced pressure
  7. concentrationThe CH2Cl2 treatment/concentration protocol
  8. customresulting amber oil
  9. waitwas stored at −20° C. for 16 h

出典と根拠

ORDレコード
ord-2f5394f539234064b469c6fd13c69670
出典データセット
uspto-grants-2014_09
特許番号
US08841330B2

関連ノート

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