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

HRID 39024

Reaction equation

HRID 39024 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-1b945c0045fd4c1786013a469ac47a59
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Linked notes

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