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

HRID 1504332노트

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HRID 1504332 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ea54609e682441489aee18255c5c80b3
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212168B2

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