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

HRID 587822Notes

Reaction equation

HRID 587822 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-7d293240499244c987a4ec77831f86e8
Source dataset
uspto-grants-2016_01
Patent number
US09227914B2

Reaction notes

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