(3-Methoxyphenyl)acetic acid → 2-(2-Bromo-5-methoxyphenyl)acetic acid

HRID 1851636Notes

Reaction equation

HRID 1851636 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.[Br:13]Br>C(Cl)Cl>[Br:13][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH2:9][C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 15719(3-Methoxyphenyl)acetic acidHCID 24408Bromine

Product 1

HCID 106340802-(2-Bromo-5-methoxyphenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-methoxyphenyl)acetic acid (4.50 g, 27.1 mmol) in DCM (25 ml), was added bromine (1.40 ml, 27.1 mmol) dropwise at 0° C. (ice-water bath). The mixture was stirred overnight at RT and quenched by addition of 5% sodium thiosulfate solution. The organic layer was washed with brine, dried with MgSO4 and concentrated under a stream of nitrogen to give the titled compound, 2-(2-bromo-5-methoxyphenyl)acetic acid as white crystalline solid.

Workup

  1. customquenched by addition of 5% sodium thiosulfate solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated under a stream of nitrogen

Sources & evidence

ORD record
ord-5d0943bd39b840f9a3b458da48410bd2
Source dataset
uspto-grants-2015_02
Patent number
US08957083B2

Reaction notes

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