Methanol → Methyl 4-fluoro-3-methylbenzoate

HRID 1617209Notes

Reaction equation

HRID 1617209 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 rt 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-0f75d67769544c5b8163af4bf016a56a
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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