Methanol → Methyl 2-bromo-2-(4-fluorophenyl)acetate

HRID 1080703Notes

Reaction equation

HRID 1080703 reaction equation
[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[CH3:13]O>>[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[C:3]([O:5][CH3:13])=[O:4]

Participants

3

Reactant 2

HCID 887MethanolHCID 16217752Bromo(4-fluorophenyl)acetic acid

Product 1

HCID 12717580Methyl 2-bromo-2-(4-fluorophenyl)acetateYield 87%

Procedure

The α-bromo-4-fluorophenylacetic acid from Part 1 was dissolved in methanol (100 ml) and was added Dowex-50X-400® (2.7 g) to the solution. The mixture was refluxed for 6 hours and the resin was removed by filtering through Celite® after cooling. The filtrate was evaporated to give an oily residue, which was purified by column chromatography on silica gel with elution by 1:9 ethyl acetate-hexane to afford methyl α-bromo-4-fluorophenylacetate (87% yield).

Workup

  1. additionwas added Dowex-50X-400® (2.7 g) to the solution
  2. temperatureThe mixture was refluxed for 6 hours
  3. customthe resin was removed
  4. filtrationby filtering through Celite®
  5. temperatureafter cooling
  6. customThe filtrate was evaporated
  7. customto give an oily residue, which
  8. customwas purified by column chromatography on silica gel with elution by 1:9 ethyl acetate-hexane

Sources & evidence

ORD record
ord-f1c151c8a57848b3b032dbab0a2ec812
Source dataset
uspto-grants-1996_12
Patent number
US05583147

Reaction notes

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