Methanol → 4-Bromo-3-fluoro-2-methylbenzoic acid

HRID 1665442Notes

Reaction equation

HRID 1665442 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[F:11].O.[CH3:13]O>S(=O)(=O)(O)O>[CH3:13][C:4]1[C:3]([F:11])=[C:2]([Br:1])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 27733414-Bromo-3-fluorobenzoic acid

Product 1

HCID 532567954-Bromo-3-fluoro-2-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

4-Bromo-3-fluorobenzoic acid (WAKO, 1.0 g) was dissolved in methanol (10 mL), followed by addition of concentrated sulfuric acid (10 drops). The mixture was refluxed for three hours. After cooling to room temperature, water was added and the extraction was carried out with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain the target compound (618 mg).

Workup

  1. temperatureThe mixture was refluxed for three hours
  2. extractionthe extraction
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-299044bc3ba543eeba9f203ba863f82b
Source dataset
uspto-grants-2011_10
Patent number
US08039514B2

Reaction notes

Loading…