Water → (3-Nitro-5-(trifluoromethyl)phenyl)methanol

HRID 217498

반응식

HRID 217498 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7](O)=[O:8])([O-:3])=[O:2].B.C1COCC1.O>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=1)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 6166023-Nitro-5-(trifluoromethyl)benzoic acidHCID 2723981Borane;tetrahydrofuran

생성물 1

HCID 18621888(3-Nitro-5-(trifluoromethyl)phenyl)methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
60 °C

실험 절차

To a solution of 3-nitro-5-(trifluoromethyl)benzoic acid (2.0 g, 8.5 mmol) in THF (100 mL) was added borane-THF (17 mL of a 1 M solution in THF, 17 mmol). The reaction was stirred at 60° C. for 24 hours and then poured into H2O (50 mL). The resultant mixture was extracted with EtOAc (100 mL) and the organic layer was washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 50% EtOAc/hexanes afforded [3-nitro-5-(trifluoromethyl)phenyl]methanol. Rf=0.35 (75% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) 8.44 (s, 1H), 8.40 (s, 1H), 7.98 (s, 1H), 4.91 (s, 2H), 2.07 (bs, 1H).

후처리

  1. extractionThe resultant mixture was extracted with EtOAc (100 mL)
  2. washthe organic layer was washed with brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography with 50% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-169e8ca2fb414140b5e24eabfa5492f4
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193365B2

연결된 노트

불러오는 중…