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

HRID 2093437Notes

Reaction equation

HRID 2093437 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-07f3f48e5c8e4f59b3223a4d0a79fbd1
Source dataset
uspto-grants-2013_05
Patent number
US08445495B2

Reaction notes

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