Methanol → Methyl 2-(3-bromophenyl)acetate

HRID 1757063Notes

Reaction equation

HRID 1757063 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:12]O>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 74653(3-Bromophenyl)acetic acid

Product 1

HCID 11746402Methyl 2-(3-bromophenyl)acetateYield 99%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

3-Bromophenyl acetic acid (2.0 g, 9.3 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 to provide 2.12 g (99%) of methyl (3-bromophenyl)acetate, which was used without further purification.

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

Sources & evidence

ORD record
ord-e29f80320e2149cd93381fe753e2b52d
Source dataset
uspto-grants-1995_08
Patent number
US05444050

Reaction notes

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