Methanol → Methyl 2-(2-bromophenyl)acetate

HRID 2108223Notes

Reaction equation

HRID 2108223 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].O.[CH3:13]O>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 877542-Bromophenylacetic acid

Product 1

HCID 8063364Methyl 2-(2-bromophenyl)acetateYield 96%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of ortho-bromophenylacetic acid (5.14 g) in dry methanol (40 ml) containing 5 drops of concentrated sulphuric acid was heated at reflux for three hours. The reaction mixture was cooled, then poured into iced water (150 ml) and extracted (2×75 ml) with ether. The ether layers were combined, washed successively with water (×3), saturated sodium bicarbonate solution (×2), water (×1) and saturated brine and then dried. Filtration and evaporation gave methyl ortho-bromophenylacetate (5.23 g, 96%) as a pale yellow liquid, IR maximum 1742 cm-1, which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for three hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted (2×75 ml) with ether
  5. washwashed successively with water (×3), saturated sodium bicarbonate solution (×2), water (×1) and saturated brine
  6. customdried
  7. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-1bd5e60cabf94618a9d54be718f12eaf
Source dataset
uspto-grants-1990_06
Patent number
US04937374

Reaction notes

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