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

HRID 39024

反応式

HRID 39024 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([Cl:12])[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.CC1C=CC(S(O[CH2:24][C@@H:25]2[O:27][CH2:26]2)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([Cl:12])[C:5]([O:11][CH2:24][CH:25]2[CH2:26][O:27]2)=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 154187Glycidyl tosylate, (R)-HCID 242119391-(5-Bromo-3-chloro-2-hydroxyphenyl)ethan-1-one

生成物 1

HCID 866529521-[5-Bromo-3-chloro-2-(oxiran-2-ylmethoxy)phenyl]ethanone収率 74.7%

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 1-(5-bromo-3-chloro-2-hydroxyphenyl)ethanone (5.5 g, 21.9 mmol), (2R)-(−)Glycidyltosylate (10 g, 43.8 mmol) and K2CO3 (4.5 g, 32.9 mmol) in DMF (25 ml) was heated at 60° C. for 25 h. 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 then dried (Na2SO4) and evaporated to dryness. Purification on flash column chromatography (isooctane/EtOAc) gave the title compound (5.0 g). MS m/z (rel. intensity, 70 eV) 250 (30), 248 (M+, 26), 235 (bp), 233 (85), 57 (90), 306 (M+, 9).

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 materialdried (Na2SO4)
  5. customevaporated to dryness
  6. customPurification on flash column chromatography (isooctane/EtOAc)

出典と根拠

ORDレコード
ord-1b945c0045fd4c1786013a469ac47a59
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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