Water → 5-Bromo-2-(oxiran-2-ylmethoxy)benzaldehyde

HRID 38982

反応式

HRID 38982 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:11]([CH:13]1[O:15][CH2:14]1)Br.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH:13]2[CH2:14][O:15]2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 728635-Bromosalicylaldehyde

生成物 1

HCID 212209825-Bromo-2-(oxiran-2-ylmethoxy)benzaldehyde収率 95.7%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

A mixture of 5-bromo-2-hydroxybenzaldehyde (10 g, 50 mmol), epibromohydrin (13.6 g, 100 mmol) and K2CO3 (10.3 g, 75 mmol) in DMF (50 ml) was heated at 60° C. for 2 h. The mixture was cooled to ambient temperature and water and EtOAc was added. The phases were separated and the combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash column chromatography (isooctane/EtOAc) to give the title compound (12.3 g). MS m/z (rel. intensity, 70 eV) 256 (M+, 41), 201 (77), 200 (bp), 199 (84), 63 (60).

後処理

  1. temperatureThe mixture was cooled to ambient temperature
  2. customThe phases were separated
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (isooctane/EtOAc)

出典と根拠

ORDレコード
ord-a41bf53d783d4cf782501d10381e2b84
出典データセット
uspto-grants-2013_09
特許番号
US08524766B2

関連ノート

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