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

HRID 38982

반응식

HRID 38982 반응식
[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]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 728635-Bromosalicylaldehyde

생성물 1

HCID 212209825-Bromo-2-(oxiran-2-ylmethoxy)benzaldehyde수율 95.7%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a41bf53d783d4cf782501d10381e2b84
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524766B2

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