Methanol → Benzoic acid, 2-bromo-5-fluoro-, methyl ester

HRID 240273Notes

Reaction equation

HRID 240273 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH3:17]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27781812-Bromo-5-fluorobenzoic acid

Product 1

HCID 138875Benzoic acid, 2-bromo-5-fluoro-, methyl ester

Procedure

To a solution of 2-bromo-5-fluorobenzoic acid (9) (21.90 g, 100 mmol) in methanol (100 mL) was added conc. H2SO4 (2 mL). The mixture was heated at reflux for 21 h. Most of the solvent was evaporated and diluted with water (200 mL). The mixture was extracted with EtOAc (150 mL×2). The combined extracts were washed with saturated NaHCO3 and brine, dried over MgSO4, and concentrated to give methyl 2-bromo-5-fluorobenzoate (10).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 21 h
  3. customMost of the solvent was evaporated
  4. additiondiluted with water (200 mL)
  5. extractionThe mixture was extracted with EtOAc (150 mL×2)
  6. washThe combined extracts were washed with saturated NaHCO3 and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-06ee322dac2f4819b3a7d07ce1db0ddb
Source dataset
uspto-grants-2014_02
Patent number
US08648073B2

Reaction notes

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