Methanol → Methyl 2-fluoro-5-methylbenzoate

HRID 2414371Notes

Reaction equation

HRID 2414371 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:16]O>>[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:16])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2428292-Fluoro-5-methylbenzoic acid

Product 1

HCID 22645471Methyl 2-fluoro-5-methylbenzoate

Procedure

To a solution of 2-fluoro-5-methylbenzoic acid (20.0 g, 0.13 mol) in MeOH (100 mL) is added thionyl chloride (1.9 mL, 26.0 mmol) dropwise, via syringe, and the solution is refluxed overnight. After cooling, the solvent is evaporated, and the residue is taken up in ethyl acetate (200 mL), extracted with sat'd aq. NaHCO3 (50 mL), brine (50 mL), water (50 mL), dried (MgSO4), and chromatographed (silica, 5% EtOAc/hexane) to yield methyl 2-fluoro-5-methylbenzoate, as a clear oil.

Workup

  1. temperaturevia syringe, and the solution is refluxed overnight
  2. temperatureAfter cooling
  3. customthe solvent is evaporated
  4. extractionextracted with sat'd aq. NaHCO3 (50 mL), brine (50 mL), water (50 mL)
  5. dry with materialdried (MgSO4)
  6. customchromatographed (silica, 5% EtOAc/hexane)

Sources & evidence

ORD record
ord-cca3d971072b4661ae3a3be906b7c4eb
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

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