2-Bromo-5-nitrophenol → 5-Amino-2-trifluoromethyl-phenol

HRID 1465145

반응식

HRID 1465145 반응식
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:11]([F:14])([F:13])[F:12])=[C:8]([OH:10])[CH:9]=1)([O-])=O.BrC1C=CC([N+]([O-])=O)=CC=1O>CO.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:11]([F:12])([F:13])[F:14])=[C:8]([OH:10])[CH:9]=1

참가 물질

5

반응물 2

HCID 128671362-Bromo-5-nitrophenolHCID 219595865-Nitro-2-(trifluoromethyl)phenol

생성물 1

HCID 159190985-Amino-2-trifluoromethyl-phenol수율 11%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

실험 절차

To a solution of 5-nitro-2-(trifluoromethyl)phenol and 2-bromo-5-nitrophenol (10 g, crude) in MeOH (60 mL) was added Raney Ni (2 g) under an atmosphere of nitrogen. The mixture was stirred under hydrogen atmosphere (1 atm) at r. t. for 4 h. The catalyst was filtered off through the celite pad and the filtrate was evaporated under vacuum. The crude product was purified by preparative HPLC to obtain 5-amino-2-(trifluoromethyl)phenol (1.7 g, 11% yield for 3 steps). 1H-NMR (400 MHz, DMSO-d6) δ 9.79 (s, 1 H), 7.04 (d, J=8.8 Hz, 1 H), 6.10 (s, 1 H), 6.01 (d, J=8.4 Hz, 1 H), 5.58 (br s, 2 H).

후처리

  1. filtrationThe catalyst was filtered off through the celite pad
  2. customthe filtrate was evaporated under vacuum
  3. customThe crude product was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-9bc1190c9db6445e97aefee3c3043a73
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999976B2

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