2-Bromophenylacetic acid → Methyl 2-(2-bromophenyl)acetate

HRID 2096595Notes

Reaction equation

HRID 2096595 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]C1C=CC(S(O)(=O)=O)=CC=1>CO>[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

4

Reactant 2

HCID 877542-Bromophenylacetic acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 8063364Methyl 2-(2-bromophenyl)acetateYield 93.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(2-bromophenyl)acetic acid (2 g, 9.3 mmol) in anhydrous methanol (20 mL) was added 4-methylbenzenesulfonic acid hydrate (1.767 g, 9.3 mmol). The mixture was heated to reflux for 3 hr. The solvent was removed in vacuum. Ethyl ether and water was added. The organic phase was washed with water and brine, then dried over Na2SO4, filtered and concentrated to give methyl 2-(2-bromophenyl)acetate (2 g, 80%), which was used for next step without purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hr
  3. customThe solvent was removed in vacuum
  4. additionEthyl ether and water was added
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-739e47827b114929b65d108920f9cd2c
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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