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

HRID 2102921Notes

Reaction equation

HRID 2102921 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([F:11])[CH:3]=1.[CH3:12][OH:13].C(N(CC)CC)C>>[CH3:12][O:13][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[F:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 27340264-Bromo-2-fluorobenzoyl chloride

Product 1

HCID 113453114-Bromo-2-fluoro-benzoic acid methyl ester

Procedure

4-Bromo-2-fluorobenzoyl chloride (45.0 g, 0.190 mol) was slowly added to a solution of methanol (31 mL, 0.76 mol) and triethylamine (53 mL, 0.38 mol) at 0° C. and the mixture was stirred at room temperature overnight. The MeOH was removed under vacuum and the residue was dissolved in CH2Cl2 (500 mL). The organic layer was washed with water, dried (Na2SO4), and concentrated to give a white solid.

Workup

  1. customThe MeOH was removed under vacuum
  2. dissolutionthe residue was dissolved in CH2Cl2 (500 mL)
  3. washThe organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give a white solid

Sources & evidence

ORD record
ord-0c81e4163e43462abfdeb349dabdd035
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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