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

HRID 1171177Notes

Reaction equation

HRID 1171177 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): 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-72b0f9b32e994cb8bb8dc439d9124210
Source dataset
uspto-grants-2010_11
Patent number
US07829594B2

Reaction notes

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