Sodium Carbonate → 4-(2-Benzyloxy ethoxy)-2-bromobenzaldehyde

HRID 1160073ノート

反応式

HRID 1160073 の反応式
[Br:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[Na+].[Na+].[CH2:17]([O:24][CH2:25][CH2:26][OH:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CS(C)=O.O>[CH2:17]([O:24][CH2:25][CH2:26][O:27][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([Br:1])[CH:9]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 121412-(Benzyloxy) ethanolHCID 27733192-Bromo-4-fluorobenzaldehyde

生成物 1

HCID 866341464-(2-Benzyloxy ethoxy)-2-bromobenzaldehyde

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
130 °C

実験手順

A mixture of 2-bromo-4-fluoro-benzaldehyde (32.0 g, 157 mmol), Na2CO3 (85.5 g, 788 mmol), and 2-benzyloxy ethanol (24.0 g, 158 mmol) in anhydrous DMSO (300 mL) were heated under N2 at 130° C. (bath temp) for 18 h. The reaction mixture cooled to rt, diluted with H2O (100 mL), and extracted with EtOAc The organic layer was washed with H2O then brine, dried (MgSO4), and concentrated in vacuo The residue was purified by flash chromatography (hexane to 10% EtOAc in hexane) to give the title compound as a viscous liquid: yield 11.8 g (22%).

後処理

  1. temperatureThe reaction mixture cooled to rt
  2. extractionextracted with EtOAc The organic layer
  3. washwas washed with H2O
  4. dry with materialbrine, dried (MgSO4)
  5. concentrationconcentrated in vacuo The residue
  6. customwas purified by flash chromatography (hexane to 10% EtOAc in hexane)

出典と根拠

ORDレコード
ord-97e05dc39e1e4f2ba99e55b96b973236
出典データセット
uspto-grants-2010_10
特許番号
US07816344B2

反応ノート

読み込み中…