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

HRID 911619Notes

Reaction equation

HRID 911619 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.S(=O)(=O)(O)O.[CH3:17]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[C:4]([F:11])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 3026814-Bromo-2-fluorobenzoic acid

Product 1

HCID 113453114-Bromo-2-fluoro-benzoic acid methyl esterYield 96%

Procedure

Dissolve 4-bromo-2-fluoro-benzoic acid (15 g, 68.5 mmol) in methanol (70 mL). Add concentrated sulfuric acid (500 μl) to the solution and heat the mixture to reflux for 20 h under a nitrogen atmosphere. Cool the mixture to room temperature and concentrate in vacuo. Dissolve the residue in EtOAc (200 mL) and wash successively with saturated aqueous NaHCO3 (50 mL) and water (2×50 mL). Dry the organic layer over Na2SO4, filter and concentrate in vacuo to obtain the desired intermediate (15.4 g, 96%). GC-MS m/z: 232 (M+).

Workup

  1. temperatureheat the mixture
  2. temperatureto reflux for 20 h under a nitrogen atmosphere
  3. concentrationconcentrate in vacuo
  4. dissolutionDissolve the residue in EtOAc (200 mL)
  5. washwash successively with saturated aqueous NaHCO3 (50 mL) and water (2×50 mL)
  6. dry with materialDry the organic layer over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-7b57f2ce4a584061b5ca4d4d33361b18
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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