Boron tribromide → 1-[2,4-Dihydroxy-3-(3-phenylpropyl)phenyl]ethanone

HRID 2210077노트

반응식

HRID 2210077 반응식
C[O:2][C:3]1[C:8]([CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:7]([O:18]C)[CH:6]=[CH:5][C:4]=1[C:20](=[O:22])[CH3:21].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[C:8]([CH2:9][CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:7]([OH:18])[CH:6]=[CH:5][C:4]=1[C:20](=[O:22])[CH3:21]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 193799231-[2,4-Dimethoxy-3-(3-phenylpropyl)phenyl]ethanone

생성물 1

HCID 193799221-[2,4-Dihydroxy-3-(3-phenylpropyl)phenyl]ethanone수율 74%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-50 °C

실험 절차

A solution of 10.0 g (33.5 mmol) of 1-[2,4-dimethoxy-3-(3-phenylpropyl)phenyl]ethanone from the preceding example in 250 mL of dichloromethane was stirred at -50° C. while 67 mL (67 mmol) of 1M boron tribromide in dichloromethane was added over a 15 min period. The reaction mixture was stirred at -50° C. for 1 hr and at room temperature for 3 days before being poured onto ice. Work-up with 9:1 dichloromethanemethanol in the usual manner gave a product which was chromatographed on silica gel. Elution with hexane-ether mixtures gave 6.69 g (74%) of the title compound as a solid. Recrystallization of a sample from ether-hexane gave colorless solid, mp 120°-122° C.

후처리

  1. additionwas added over a 15 min period
  2. additionbefore being poured onto ice
  3. customgave a product which
  4. customwas chromatographed on silica gel
  5. washElution with hexane-ether mixtures

출처 및 근거

ORD 기록
ord-507fdc5fea7f46adaa8904fd75e59983
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05457124

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