Methanol → Methyl 4-fluoro-3-methylbenzoate

HRID 2387861Notes

Reaction equation

HRID 2387861 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[CH3:15].[CH3:16]O>>[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][CH3:16])=[O:11])=[CH:8][C:7]=1[CH3:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2428284-Fluoro-3-methylbenzoic acid

Product 1

HCID 18788764Methyl 4-fluoro-3-methylbenzoate

Procedure

Thionyl chloride (5.68 ml) was added dropwise to a solution of 4-fluoro-3-methylbenzoic acid (10 g) in MeOH (150 mL) at 0° C. over a period of 10 minutes under nitrogen. The resulting mixture was stirred at It for 24 h. The solvent was removed and the residue diluted with EtOAc, washed with sat. NaHCO3, brine, dried, filtered and evaporated to afford the subtitle compound, 9.85 g.

Workup

  1. customThe solvent was removed
  2. additionthe residue diluted with EtOAc
  3. washwashed with sat. NaHCO3, brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-9757d791668a497c95aacbabe3e09ab0
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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