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

HRID 38999

反応式

HRID 38999 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

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 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).

後処理

  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)

出典と根拠

ORDレコード
ord-2c0dfc5a21934582bc955561daae8b21
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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