Methanol → 4-Bromo-2-fluoro-benzoic acid methyl ester

HRID 415141Notes

Reaction equation

HRID 415141 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1.[CH3:12]O>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:12])=[O:7])=[C:4]([F:11])[CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 3026814-Bromo-2-fluorobenzoic acid

Product 1

HCID 113453114-Bromo-2-fluoro-benzoic acid methyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

4-bromo-2-fluorobenzoic acid (30 g, 0.14 mol) was dissolved in methanol with a few drops of sulfuric acid. The reaction medium was refluxed for 20 hours. The cooled reaction mixture was evaporated and the residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic layer was separated and washed with brine, dried over sodium sulfate, filtered and evaporated to give methyl 4-bromo-2-fluorobenzoate (20.7 g, yield 64%) as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm); 3.85 (s, 3H), 7.55-7.58 (m, 1H), 7.70-7.73 (m, 1H), 7.79-7.83 (m, 1H); LC-MS (ESI) m/z: 233 (M+1)+, 235 (M+3)+

Workup

  1. temperatureThe reaction medium was refluxed for 20 hours
  2. customThe cooled reaction mixture
  3. customwas evaporated
  4. customthe residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-4b2b8c4a2cf84a899e0e67555e8150c0
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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