Methanol → Methyl 2-(4-bromophenyl)acetate

HRID 2185043Notes

Reaction equation

HRID 2185043 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.S(=O)(=O)(O)O.[CH3:17]O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:17])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

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

Product 1

HCID 316783Methyl 2-(4-bromophenyl)acetate

Procedure

A solution of 4-bromophenylacetic acid (10.0 g, 46.5 mmol), in methanol (125 mL) and sulfuric acid (5 mL) was heated at reflux overnight. The reaction mixture was concentrated and partitioned between ethyl ether and saturated aqueous sodium bicarbonate. The organic layer was washed with water and brine, then dried over magnesium sulfate. The organic layer was filtered and evaporated to an oil to afford the title compound.

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between ethyl ether and saturated aqueous sodium bicarbonate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe organic layer was filtered
  7. customevaporated to an oil

Sources & evidence

ORD record
ord-75d1b6a39805442581e62d2794cd0841
Source dataset
uspto-grants-2002_06
Patent number
US06399640B1

Reaction notes

Loading…