Boron tribromide → 1-(5-chloro-2-hydroxy-4-methyl-3-nitrophenyl)ethanone

HRID 510825노트

반응식

HRID 510825 반응식
[Cl:1][C:2]1[C:3]([CH3:16])=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([O:11]C)=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:3]([CH3:16])=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 27576391-(5-Chloro-2-methoxy-4-methyl-3-nitrophenyl)ethanone

생성물 1

HCID 27576081-(5-chloro-2-hydroxy-4-methyl-3-nitrophenyl)ethanone

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
-78 °C

실험 절차

To a mixture of 1-(5-chloro-2-methoxy-4-methyl-3-nitrophenyl)ethanone (8.9 g, 37 mmol, from Oakwood) in methylene chloride (200 mL) was added 1.0 M boron tribromide in methylene chloride (38.4 mL, 38.4 mmol) at −78° C. After stirring at −78° C. for 10 minutes, the reaction was allowed to warm up to 0° C., quenched with water at 0° C., and extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate and filtered. After evaporating to dryness under reduced pressure, the residue was used directly in next step (8.2 g, 98%). LCMS calculated for C9H9ClNO4 (M+H)+: m/z=230.0. found: 230.1.

후처리

  1. temperatureto warm up to 0° C.
  2. customquenched with water at 0° C.
  3. extractionextracted with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customAfter evaporating to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-fbfaa6712b7c473e897042a074ae24ed
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096600B2

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