Water → 2-Bromo-5-methoxybenzoic acid

HRID 497981Notes

Reaction equation

HRID 497981 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].[Br:12]Br.O>C(O)(=O)C>[Br:12][C:9]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 114613-Methoxybenzoic AcidHCID 24408Bromine

Product 1

HCID 899062-Bromo-5-methoxybenzoic acidYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

The title compound was prepared according to the method described in JP 63-287756 A. To a solution of 3-methoxybenzoic acid (25.0 g, 164 mmol) in acetic acid (150 mL), a solution of bromine (26.5 g, 166 mmol) in acetic acid (75 mL) was added dropwise at room temperature, and the mixture was stirred at the same temperature for 8 hours. The mixture was poured into water, and the resulting crystals were collected by filtration, washed with water, and air dried to give the title compound (29.5 g, 78% yield).

Workup

  1. customThe title compound was prepared
  2. filtrationthe resulting crystals were collected by filtration
  3. washwashed with water, and air
  4. customdried

Sources & evidence

ORD record
ord-6e23b867c0f44b5da5399738ed33d3f7
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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