p-Toluenesulfonic acid → Methyl 2-fluorophenylacetate

HRID 1419495Notes

Reaction equation

HRID 1419495 reaction equation
[C:1]1(C)C=CC(S(O)(=O)=O)=CC=1.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]([OH:22])=[O:21]>CO>[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]([O:22][CH3:1])=[O:21]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 67979Benzeneacetic acid, 2-fluoro-

Product 1

HCID 2733230Methyl 2-fluorophenylacetateYield 22,016.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

p-Toluenesulfonic acid (20 mg) was added to a solution of 2-fluorophenyl acetic acid (3.8 g, 24.65 mmol) in methanol (29 ml). After heating the reaction mixture for 1 h on the steam bath, the solvent was removed in vacuo. Filtration through a pad of silica gel (ethyl acetate/hexanes 10/90) gave methyl 2-fluorophenylacetate (4.3 g) as an oil.

Workup

  1. temperatureAfter heating the reaction mixture for 1 h on the steam bath
  2. customthe solvent was removed in vacuo
  3. filtrationFiltration through a pad of silica gel (ethyl acetate/hexanes 10/90)

Sources & evidence

ORD record
ord-819dedee4f5647b3b1db7df374e70f86
Source dataset
uspto-grants-1999_03
Patent number
US05886178

Reaction notes

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