Methanol → Methyl 2,6-difluoro-3-methylbenzoate

HRID 539708Notes

Reaction equation

HRID 539708 reaction equation
[F:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]([F:12])[C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:17]O>>[F:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]([F:12])[C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27741422,6-Difluoro-3-methylbenzoic acid

Product 1

HCID 55255639Methyl 2,6-difluoro-3-methylbenzoateYield 86%

Procedure

To a 0° C. solution of 2,6-difluoro-3-methylbenzoic acid (10.0 g, 58.1 mmol, 1.0 equiv) in dry methanol (100 mL) was added dropwise thionyl chloride (4.64 mL, 63.9 mmol, 1.1 equiv). The resulting solution was refluxed overnight. After the reaction mixture was allowed to cool to room temperature, the solvent was removed in vacuo. The product was dissolved in ethyl acetate and washed with aq. satd. NaHCO3. The EtOAc layer was dried over sodium sulfate, filtered and concentrated in vacuo to provide the desired ester (9.35 g, 86%).

Workup

  1. temperatureThe resulting solution was refluxed overnight
  2. customthe solvent was removed in vacuo
  3. dissolutionThe product was dissolved in ethyl acetate
  4. washwashed with aq. satd
  5. dry with materialThe EtOAc layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3d28edd348ad40fd9fc64e3aa06bafd6
Source dataset
uspto-grants-2014_10
Patent number
US08871768B2

Reaction notes

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