Methanol → Methyl 3-bromobenzoate

HRID 54195

Reaction equation

HRID 54195 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:11]O>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:11])=[O:6]

Participants

4

Reactant 2

HCID 887MethanolHCID 114563-Bromobenzoic acid

Product 1

HCID 12070Methyl 3-bromobenzoateYield 85%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

Part A: 3-Bromobenzoic acid (1.1 g, 5.47 mmol) was dissolved in methanol (20 ml) in a 50 ml flask. Concentrated sulfuric acid (2 drops) was added and the mixture was refluxed under nitrogen for ten hours then concentrated under reduced pressure. The residue was mixed with dichloromethane (20 ml) and saturated sodium bicarbonate solution (10 ml). The organic material was separated, dried (MgSO4) and concentrated under reduced pressure. The residue was flushed through silica gel with hexane/ethyl acetate (3:1), and concentrated which provided methyl 3-bromobenzoate (1.0 g, 85%).

Workup

  1. temperaturethe mixture was refluxed under nitrogen for ten hours
  2. concentrationthen concentrated under reduced pressure
  3. additionThe residue was mixed with dichloromethane (20 ml) and saturated sodium bicarbonate solution (10 ml)
  4. customThe organic material was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was flushed through silica gel with hexane/ethyl acetate (3:1)
  8. concentrationconcentrated which

Sources & evidence

ORD record
ord-02beae4f681d488aae48056e2215c553
Source dataset
uspto-grants-1997_04
Patent number
US05622937

Linked notes

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