Boron tribromide → 4-Hydroxy-2,5-dimethyl-benzaldehyde

HRID 2108601ノート

反応式

HRID 2108601 の反応式
[CH3:1][C:2]1[CH:9]=[C:8]([O:10]C)[C:7]([CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5].B(Br)(Br)Br>C(Cl)Cl>[CH3:1][C:2]1[CH:9]=[C:8]([OH:10])[C:7]([CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 812274-Methoxy-2,5-dimethylbenzaldehyde

生成物 1

HCID 128272904-Hydroxy-2,5-dimethyl-benzaldehyde収率 57.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

First step: To a stirring solution of 2,5-dimethyl-4-methoxybenzaldehyde (0.82 g, 5.0 mmol) at −20° C. in CH2Cl2 (10 mL) was added BBr3 (10 mL, 1M in CH2Cl2). The reaction mixture was stirred at room temperature for 16 hrs. It was added ice and diluted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with ethyl acetate/hexanes (1:1) to afford 2,5-dimethyl-4-hydroxy-benzaldehyde as a yellow solid (0.43 g, 57%): 1H NMR (300 MHz, DMSO-d6): δ 10.41 (s, 1H), 9.99 (s, 1H), 7.56 (s, 1H), 6.69 (s, 1H), 2.51 (s, 3H), 2.14 (s, 3H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=20% ethyl acetate in hexanes; Rf=0.48.

後処理

  1. additionIt was added ice
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel
  6. washeluting with ethyl acetate/hexanes (1:1)

出典と根拠

ORDレコード
ord-5006efafac9f46bab7c3fb70369b8ed1
出典データセット
uspto-grants-2009_04
特許番号
US07514419B2

反応ノート

読み込み中…