Hydrogen Bromide → 2-Bromo-3-methoxybenzoic acid

HRID 906095Notes

Reaction equation

HRID 906095 reaction equation
N[C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].N([O-])=O.[Na+].[BrH:17]>O.[Cu]Br>[Br:17][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 260Hydrogen Bromide2×HCID 2557202-Amino-3-methoxybenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 1451622-Bromo-3-methoxybenzoic acidYield 74%

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To 2-amino-3-(methyloxy)benzoic acid (4.00 g, 23.9 mmol) in 10% aqueous hydrobromic acid (54 ml) at 0° C. was added sodium nitrite (1.65 g, 23.9 mmol) in water (17 ml). To this solution was added dropwise a solution of copper (I) bromide (3.78 g, 26.3 mmol) in 48% hydrobromic acid (22 ml) and heated to 60° C. for 2 h. The mixture was cooled to 0° C., and the resultant precipitate was collected by filtration, washed with cold water and recrystallized from water to give pure 2-bromo-3-(methyloxy)benzoic acid (4.07 g, 74%). MS (EI) for C8H7BrO3: 232 (MH+).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. filtrationthe resultant precipitate was collected by filtration
  3. washwashed with cold water
  4. customrecrystallized from water

Sources & evidence

ORD record
ord-de900013b4604ab982812d52fc2ead09
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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