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

HRID 510825ノート

反応式

HRID 510825 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fbfaa6712b7c473e897042a074ae24ed
出典データセット
uspto-grants-2015_08
特許番号
US09096600B2

反応ノート

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