Sodium Carbonate → 2-Benzyloxy propoxy-2-bromobenzaldehyde

HRID 339626ノート

反応式

HRID 339626 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][CH:25]([CH3:28])[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][CH:25]([CH3:28])[CH2:26][O:27][C:9]1[C:2]([Br:1])=[C:3]([CH:6]=[CH:7][CH:8]=1)[CH:4]=[O:5])[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 5618252-(Benzyloxy)propan-1-olHCID 27733192-Bromo-4-fluorobenzaldehyde

生成物 1

HCID 866341472-Benzyloxy propoxy-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 (30.0 g, 148 mmol), Na2CO3 (78.31 g, 738.8 mmol) and 2-benzyloxy propanol (24.56 g, 147.8 mmol) in anhydrous DMSO (300 mL) was heated with stirring at 130° C. (bath temp) for 72 h under N2. The reaction mixture was cooled to rt and diluted with H2O 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 30% EtOAc in hexane) to give the title compound: yield 3.84 g (7%).

後処理

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled to rt
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with H2O
  5. dry with materialbrine, dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (hexane to 30% EtOAc in hexane)

出典と根拠

ORDレコード
ord-3af1b686eead4d5a8969e3b6016b1e49
出典データセット
uspto-grants-2014_11
特許番号
US08895534B2

反応ノート

読み込み中…