3-(Trifluoromethyl)aniline → 2-bromo-N-[3-(trifluoromethyl)phenyl]acetamide

HRID 1371562

반응식

HRID 1371562 반응식
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].CCN(C(C)C)C(C)C.[Br:21][CH2:22][C:23](Cl)=[O:24]>ClCCl>[Br:21][CH2:22][C:23]([NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=1)=[O:24]

참가 물질

5

반응물 3

HCID 73753-(Trifluoromethyl)anilineHCID 81531DiisopropylethylamineHCID 89602Bromoacetyl chloride

생성물 1

HCID 23171522-bromo-N-[3-(trifluoromethyl)phenyl]acetamide수율 64%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

3-Trifluoromethylaniline (1.6 g, 10 mmol) was dissolved in dichloromethane with DIEA (3.4 mL, 20 mmol), cooled to 0° C., and to this solution bromoacetyl chloride was added as a neat liquid (exothermic). After 1 hour the reaction mixture was washed with 1N HCl, dried and concentrated to a brown oil which was purified by column chromatography (10 to 40% EtOAc/hexanes) to give a light brown oil, 1.8 g, 6.4 mmol, 64% yield. 1H NMR (500 MHz, CDCl3) δ 8.19 (s, 1H), 7.75 (s, 1H), 7.68 (d, J=8.1 Hz, 1H), 7.41 (t, J=7.9 Hz, 1H), 7.35 (d, J=7.8 Hz, 3.96 (s, 2H).

후처리

  1. washAfter 1 hour the reaction mixture was washed with 1N HCl
  2. customdried
  3. concentrationconcentrated to a brown oil which
  4. customwas purified by column chromatography (10 to 40% EtOAc/hexanes)
  5. customto give a light brown oil, 1.8 g, 6.4 mmol, 64% yield

출처 및 근거

ORD 기록
ord-9d54cb18bf4945e39b0b7c92546e01a5
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157476B2

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