Methanol → Methyl 3,5-difluorobenzoate

HRID 875388Notes

Reaction equation

HRID 875388 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5]([OH:7])=[O:6].[C:12](Cl)(=O)C(Cl)=O.CN(C)C=O.CO>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5]([O:7][CH3:12])=[O:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 1012653,5-Difluorobenzoic acid

Product 1

HCID 2775360Methyl 3,5-difluorobenzoateYield 91.91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,5-difluorobenzoic acid (10 gm, 63.2 mmol) in dichloromethane (100 mL) was added oxalyl chloride (11.96 gm, 94.9 mmol) at 0° C. followed by addition of dimethylformamide (2 mL). The resulting reaction mixture was stirred for about 3 hours at room temperature. Methanol (100 mL) was added to the reaction mass and stirring was continued further for 20-30 minutes. Solvents were evaporated to obtain an oily mass which was further purified by column chromatography over silica gel (100-200) using ethyl acetate/hexane gradient elution to afford colorless methyl 3,5-difluorobenzoate (10 gm, 91.91%).

Workup

  1. customThe resulting reaction mixture
  2. stirringstirring
  3. waitwas continued further for 20-30 minutes
  4. customSolvents were evaporated
  5. customto obtain an oily mass which
  6. customwas further purified by column chromatography over silica gel (100-200)
  7. washethyl acetate/hexane gradient elution

Sources & evidence

ORD record
ord-2c79545194114172b8c95b2a97e64847
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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