Methanol → Methyl 2-(4-bromophenyl)acetate

HRID 547980Notes

Reaction equation

HRID 547980 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:17]O>>[CH3:17][O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 316783Methyl 2-(4-bromophenyl)acetate

Procedure

(4-bromophenyl)acetic acid (10 g, 1 eq) was dissolved in methanol. 10 ml conc. H2SO4 was added into the solution and the mixture was heated and refluxed for 3 hours. When the reaction was completed, the mixture was vacuum distilled and extracted with ethyl acetate and water. After the organic layer was washed with saturated NaHCO3, the target compound (4-bromophenyl)acetic acid methyl ester was obtained by drying the layer with anhydrous magnesium sulfate and removing the solvent at low pressures (9.87 g, 93%).

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 3 hours
  3. distillationdistilled
  4. extractionextracted with ethyl acetate and water
  5. washAfter the organic layer was washed with saturated NaHCO3

Sources & evidence

ORD record
ord-9cbc8f2617614823b1237e325342fc24
Source dataset
uspto-grants-2011_05
Patent number
US07939672B2

Reaction notes

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