Methanol → Methyl 3-Bromo-2-methylbenzoate

HRID 908289Notes

Reaction equation

HRID 908289 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].OS(O)(=O)=O.[CH3:17]O>>[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:17])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27355903-Bromo-2-methylbenzoic Acid

Product 1

HCID 12929135Methyl 3-Bromo-2-methylbenzoateYield 98%

Procedure

3-bromo-2-methylbenzoic acid (6.13 g, 28.5 mmol) was suspended in MeOH (52 ml) and concentrated H2SO4 (10.0 ml) was added via syringe over 4 minutes at room temperature. The reaction was heated to 90 C, stirred for 4 hours, cooled in an ice water bath, and then quenched with saturated NaHCO3 (250 ml). The reaction was extracted with EtOAc (3×50 ml), and the organic layers were combined, dried over MgSO4, filtered, and concentrated to give methyl 3-bromo-2-methylbenzoate (6.43 g, 98%).

Workup

  1. temperatureThe reaction was heated to 90 C
  2. temperaturecooled in an ice water bath
  3. customquenched with saturated NaHCO3 (250 ml)
  4. extractionThe reaction was extracted with EtOAc (3×50 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-20cd4dbaea7c48669f45e82264f52c6f
Source dataset
uspto-grants-2011_09
Patent number
US08017601B2

Reaction notes

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