Acetone → 4-Bromo-2,3-difluoro-oxiranylmethoxy benzene

HRID 2109135Notes

Reaction equation

HRID 2109135 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[C:3]=1[F:10].C(=O)([O-])[O-].[K+].[K+].[CH3:17][C:18]([CH3:20])=[O:19]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][CH:18]2[CH2:20][O:19]2)=[C:4]([F:9])[C:3]=1[F:10]

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 102199424-Bromo-2,3-difluorophenol

Product 1

HCID 866038934-Bromo-2,3-difluoro-oxiranylmethoxy benzeneYield 71%

Procedure

A solution of the crude 4-bromo-2,3-difluorophenol (0.40 g) [prepared using published procedure, WO0121606] and (2R)-glycidyl 3-nitrobenzenesulfonate (0.49 g) in dry acetone (19 mL) was treated with potassium carbonate (0.79 g) and refluxed under nitrogen for 12 h. The reaction was cooled, filtered and filtrate was concentrated in vacuo and the residue was flash chomatogaphed (20% ethyl acetate/hexanes) to yield the desired product (0.33 g) in 71% yield. 1H-NMR (400 MHz, CDCl3) : 7.23-7.19 (m, 1H), 6.74-6.71 (m, 1H), 4.35-4.32 (m, 1H), 4.03-3.99 (m, 1H), 3.38-3.35 (m, 1H), 2.93-2.92 (m, 1H), 2.77-2.76 (m, 1H).

Workup

  1. temperaturerefluxed under nitrogen for 12 h
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. concentrationfiltrate was concentrated in vacuo

Sources & evidence

ORD record
ord-43cbcf7f31a34116af50e5da97d2bf5d
Source dataset
uspto-grants-2009_04
Patent number
US07514473B2

Reaction notes

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