Methanol → Methyl 2-Bromo-4-chlorobenzoate

HRID 1644678Notes

Reaction equation

HRID 1644678 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH3:17]O>>[CH3:17][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:7]=1[Br:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 331262-Bromo-4-chlorobenzoic acid

Product 1

HCID 15110995Methyl 2-Bromo-4-chlorobenzoateYield 98%

Procedure

Concentrated sulfuric acid (5 mL) was added drop-wise to an ice-cold mixture of 2-bromo-4-chloro-benzoic acid (10.14 g, 0.0431 mol) and methanol (40 mL). The resulting mixture was heated at reflux for 17 hours. After this time, the reaction mixture was cooled to room temperature, and then poured into ice-cold water (150 mL), creating a white suspension. The suspension was extracted with ethyl acetate (150 mL). The organic phase was washed with saturated aqueous NaHCO3 (100 mL), followed by saturated aqueous NaCl (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to afford 2-bromo-4-chloro-benzoic acid methyl ester (10.57 g, 98% yield) as a clear oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 17 hours
  3. extractionThe suspension was extracted with ethyl acetate (150 mL)
  4. washThe organic phase was washed with saturated aqueous NaHCO3 (100 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dd9bfac4059f4d319fe1e5d6bbf9a793
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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