Methanol → Methyl (2,4-difluorophenyl)acetate

HRID 880618Notes

Reaction equation

HRID 880618 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[CH2:14][C:15]([OH:17])=[O:16].[CH3:18]O>>[F:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[CH2:14][C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1235812,4-Difluorophenylacetic acid

Product 1

HCID 50998344Methyl (2,4-difluorophenyl)acetate

Procedure

Sulfuric acid (3.35 mL) was added to a stirred solution of 2,4-difluorophenylacetic acid ([CAS 81228-09-3], 3.5 g, 20.33 mmol) in MeOH (70 mL) at RT. The mixture was stirred at reflux for 18 h. The methanol was removed in vacuo. The residue was diluted with EtOAc and washed successively with H2O, sat. aq. NaHCO3 and brine. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo to yield I-24 (3.34 g, 88%) as a light yellow oil.

Workup

  1. temperatureat reflux for 18 h
  2. customThe methanol was removed in vacuo
  3. additionThe residue was diluted with EtOAc
  4. washwashed successively with H2O, sat. aq. NaHCO3 and brine
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo
  9. customto yield I-24 (3.34 g, 88%) as a light yellow oil

Sources & evidence

ORD record
ord-28290b13c1774e2393637f42312247e1
Source dataset
uspto-grants-2015_03
Patent number
US08993591B2

Reaction notes

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