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

HRID 2043553Notes

Reaction equation

HRID 2043553 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) δ: 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-3a7c48f6adc14d23baf386486df403a2
Source dataset
uspto-grants-2013_11
Patent number
US08586631B2

Reaction notes

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