Methanol → Methyl 2,3-difluorobenzoate

HRID 1695926Notes

Reaction equation

HRID 1695926 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH3:17]O>>[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 3705902,3-Difluorobenzoic acid

Product 1

HCID 2782927Methyl 2,3-difluorobenzoate

Procedure

2,3-difluorobenzoic acid (9.47 g, 59.90 mmol) and H2SO4 (0.3 mL) in methanol (100 mL) were heated for 3 days in a 70° C. oil bath. The reaction was cooled to RT, then the solvent was removed under vacuum at 35° C. The crude residue was transferred to a separatory funnel with ether, washed with saturated sodium bicarbonate solution (2×50 mL), brine, dried (MgSO4), filtered and concentrated under vacuum. The residue was redissolved in CH2Cl2, dried (MgSO4), filtered and concentrated under vacuum to yield 8.66 grams of methyl 2,3-difluorobenzoate as a clear liquid.

Workup

  1. customthe solvent was removed under vacuum at 35° C
  2. customThe crude residue was transferred to a separatory funnel with ether
  3. washwashed with saturated sodium bicarbonate solution (2×50 mL), brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. dissolutionThe residue was redissolved in CH2Cl2
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-af0107e7c37b404f973de14fa5c2d968
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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