Methanol → 2-(3-Benzyl-4,4,4-trifluoro-3-hydroxy-1,1-dimethylbutyl)-4-fluorophenol

HRID 916007노트

반응식

HRID 916007 반응식
[CH2:1]([C:8]([OH:26])([CH2:13][C:14]([C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[O:24]C)([CH3:16])[CH3:15])[C:9]([F:12])([F:11])[F:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.CO>ClCCl.O>[CH2:1]([C:8]([OH:26])([C:9]([F:10])([F:12])[F:11])[CH2:13][C:14]([C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[OH:24])([CH3:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 887MethanolHCID 25134Boron tribromideHCID 102372232-Benzyl-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol

생성물 1

HCID 589599242-(3-Benzyl-4,4,4-trifluoro-3-hydroxy-1,1-dimethylbutyl)-4-fluorophenol수율 66.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 49 mg (0.13 mmol) of 2-benzyl-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol (Example 4) in 0.5 mL of dichloromethane, 1 mL (1.0 mmol) of 1 M solution of boron tribromide in dichloromethane was added. The mixture was stirred at room temperature for 3 hours and was then cautiously added to cold MeOH and stirred for 20 minutes. The mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with saturated aqueous sodium bicarbonate, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude residue was chromatographed on silica gel using first hexanes then EtOAc-hexanes (0.5:99.5 to 1:99) to afford 31 mg (65%) of the title compound as a clear oil.

후처리

  1. stirringstirred for 20 minutes
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was chromatographed on silica gel using first hexanes

출처 및 근거

ORD 기록
ord-dda5af2e852a4b80819f0ced98d3bb46
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268152B2

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