Hydrochloric Acid → 4-Bromo-2-methoxybenzoic acid

HRID 1803935Notes

Reaction equation

HRID 1803935 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[OH-].[Na+].Cl>CO>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15128242Methyl 4-bromo-2-methoxybenzoate

Product 1

HCID 134507554-Bromo-2-methoxybenzoic acidYield 97.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-bromo-2-methoxybenzoate (10 g) was dissolved in methanol (80 mL), 1N aqueous sodium hydroxide solution (80 mL) was added, and the mixture was refluxed for 3 hr. After cooling, 1N hydrochloric acid (80 mL) was added, and the mixture was filtered to give 4-bromo-2-methoxybenzoic acid (9.2 g). By reaction and treatment in the same manner as in Preparation Example 1 and using 4-bromo-2-methoxybenzoic acid (3.1 g) and 1-(2,4-dimethylphenyl)piperazine (2.7 g), the title compound (4.4 g) was obtained.

Workup

  1. temperaturethe mixture was refluxed for 3 hr
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-308fb008b2434e7ca3ed5064679437d5
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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