Water → 1-[5-Bromo-3-fluoro-2-(oxiran-2-ylmethoxy)phenyl]ethanone

HRID 38999

반응식

HRID 38999 반응식
[Br:1][C:2]1[CH:3]=[C:4]([F:12])[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH2:13]([CH:15]1[O:17][CH2:16]1)Br.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([F:12])[C:5]([O:11][CH2:13][CH:15]2[CH2:16][O:17]2)=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 575158461-(5-Bromo-3-fluoro-2-hydroxyphenyl)ethan-1-one

생성물 1

HCID 866529431-[5-Bromo-3-fluoro-2-(oxiran-2-ylmethoxy)phenyl]ethanone수율 85.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

A mixture of 1-(5-bromo-3-fluoro-2-hydroxyphenyl)ethanone (3.7 g, 15.8 mmol), epibromohydrin (2.6 ml, 31.7 mmol) and K2CO3 (3.3 g, 23.8 mmol) in DMF (20 ml) was heated at 60° C. for 1 h 50 min. The solution was brought to ambient temperature and water and EtOAc was added. The water phase was extracted with EtOAc. The combined organic phases were washed with LiCl (5%), HCl (1 N) and brine and were dried (Na2SO4) and evaporated to dryness. Purification on flash column chromatography (isooctane/EtOAc) gave the title compound (3.9 g). MS m/z (rel. intensity, 70 eV) 289 (M+, 13), 288 (M+, 14), 218 (91), 217 (bp), 81 (39), 57 (95).

후처리

  1. customwas brought to ambient temperature
  2. extractionThe water phase was extracted with EtOAc
  3. washThe combined organic phases were washed with LiCl (5%), HCl (1 N) and brine
  4. dry with materialwere dried (Na2SO4)
  5. customevaporated to dryness
  6. customPurification on flash column chromatography (isooctane/EtOAc)

출처 및 근거

ORD 기록
ord-2c0dfc5a21934582bc955561daae8b21
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524766B2

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