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

HRID 39004

Reaction equation

HRID 39004 reaction equation
[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](OS(C1C=CC(C)=CC=1)(=O)=O)[C@@H:14]1[O:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([F:12])[C:5]([O:11][CH2:13][C@H:14]2[CH2:15][O:16]2)=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 154187Glycidyl tosylate, (R)-HCID 575158461-(5-Bromo-3-fluoro-2-hydroxyphenyl)ethan-1-one

Product 1

HCID 866529451-(5-Bromo-3-fluoro-2-[(2R)-oxiran-2-ylmethoxy]phenyl) ethanoneYield 39.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Preparation according to Preparation 1 using 1-(5-bromo-3-fluoro-2-hydroxyphenyl)ethanone (16.8 g, 72 mmol), (R)-glycidyltosylate (18.1 g, 79 mmol), K2CO3 (15.0 g, 108 mmol) and DMF (60 ml). The combined organic phases were washed with LiCl (5%), HCl (1 N). Flash column chromatography (isooctane/EtOAc) yielded the title compound (8.3 g). MS m/z (rel. intensity, 70 eV) 290 (M+, 9), 288 (M+, 9), 217 (bp), 81 (47), 57 (46).

Workup

  1. customPreparation
  2. washThe combined organic phases were washed with LiCl (5%), HCl (1 N)

Sources & evidence

ORD record
ord-c4f7e5f0653e424aadb321dbd738c539
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Linked notes

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