Bromine → 3-(3-Bromo-4-methoxyphenyl)propanoic acid

HRID 582202

Reaction equation

HRID 582202 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.[Br:14]Br>C(O)(=O)C.O>[Br:14][C:8]1[CH:7]=[C:6]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 24408BromineHCID 957503-(p-Methoxyphenyl)propionic acid

Product 1

HCID 45476083-(3-Bromo-4-methoxyphenyl)propanoic acidYield 87%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 3-(4-methoxyphenyl)propionic acid (4.0 g, 22.2 mmol) in acetic acid (20 ml) was added bromine (3.9 g, 24.4 mmol) gradually dropwise at 10° C. and the mixture was stirred at room temperature for 30 minutes. This reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed serially with saturated saline and water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was washed with hexane to provide the title compound (yield 5.0 g, 87%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed serially with saturated saline and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-5ecfdcfbe9494c28b0be488c71647880
Source dataset
uspto-grants-1999_07
Patent number
US05922771

Linked notes

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