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

HRID 39024

반응식

HRID 39024 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

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).

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

출처 및 근거

ORD 기록
ord-1b945c0045fd4c1786013a469ac47a59
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524766B2

연결된 노트

불러오는 중…