N-bromobutanimide → 4-Bromo-2-fluoro-3-(trifluoromethoxy)aniline

HRID 1504332ノート

反応式

HRID 1504332 の反応式
[F:1][C:2]1[C:8]([O:9][C:10]([F:13])([F:12])[F:11])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[Br:14]N1C(=O)CCC1=O>CN(C=O)C>[Br:14][C:7]1[CH:6]=[CH:5][C:3]([NH2:4])=[C:2]([F:1])[C:8]=1[O:9][C:10]([F:11])([F:12])[F:13]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 252105032-Fluoro-3-(trifluoromethoxy)aniline

生成物 1

HCID 866828084-Bromo-2-fluoro-3-(trifluoromethoxy)aniline収率 90.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of 2-fluoro-3-(trifluoromethoxy)aniline (1.0 g, 5.13 mmol) dissolved in DMF (2 mL) at 0° C. was slowly added a solution of cold N-bromosuccinimide (0.91 g, 5.13 mmol) dissolved in DMF (6 mL) over 5 min. The reaction mixture was stirred at 0° C. for 1 h, extracted with EtOAc (125 mL) and washed with water (3×25 mL). The combined aqueous layers were extracted with EtOAc (75 mL). The combined organic layers were washed with brine (25 mL), dried over sodium sulfate, filtered, and concentrated to produce the title compound as a dark colored liquid (1.27 g, 90% yield). (m/z): [M+H]+ calcd for C7H4BrF4NO 273.94. found 273.8.

後処理

  1. extractionextracted with EtOAc (125 mL)
  2. washwashed with water (3×25 mL)
  3. extractionThe combined aqueous layers were extracted with EtOAc (75 mL)
  4. washThe combined organic layers were washed with brine (25 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-ea54609e682441489aee18255c5c80b3
出典データセット
uspto-grants-2015_12
特許番号
US09212168B2

反応ノート

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