Acetone → (R)-2-(5-Bromo-2-fluoro-phenoxymethyl)-oxirane

HRID 874790Notes

Reaction equation

HRID 874790 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:16][C:17]([CH3:19])=[O:18]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([CH:7]=1)[O:8][CH2:16][C@H:17]1[CH2:19][O:18]1

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 183421Phenol, 5-bromo-2-fluoro-

Product 1

HCID 86603895(R)-2-(5-Bromo-2-fluoro-phenoxymethyl)-oxiraneYield 82%

Procedure

A solution of the crude 5-bromo-2-fluorophenol (4.0 g) prepared using literature procedure [EP0238272] and (2R)-glycidyl 3-nitrobenzenesulfonate (5.37 g) in dry acetone (175 mL) was treated with potassium carbonate (8.58 g) and refluxed under nitrogen for 12 h. The reaction was cooled, filtered and filtrate was concentrated in vacuo and the residue was flash chromatographed (20% ethyl acetate/hexanes) to yield the desired product (4.25 g) in 82% yield. 1H NMR (400 MHz, CDCl3): δ 7.15-6.96 (m, 3H), 4.33 and 4.30 (dd, 1H), 4.02 and 4.00 (dd, 1H), 3.41-3.37 (m, 1H), 2.97 (m, 1H), 2.78 (m, 1H).

Workup

  1. temperaturerefluxed under nitrogen for 12 h
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. concentrationfiltrate was concentrated in vacuo
  5. customchromatographed (20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-95fa5f9a89354c52804a3ca6c07e902e
Source dataset
uspto-grants-2015_03
Patent number
US08980950B2

Reaction notes

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