Hydrochloric Acid → 4-Bromo-3-methoxybenzoic acid

HRID 1244777Notes

Reaction equation

HRID 1244777 reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([O:11][CH3:12])[CH:5]=1.C1COCC1.CO.[OH-].[Li+].Cl>O>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:13])=[O:2])=[CH:5][C:6]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 14570117Methyl 4-bromo-3-methoxybenzoateHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 162158674-Bromo-3-methoxybenzoic acidYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-bromo-3-methoxy-benzoic acid methyl ester (6.875 mmol, 1.676 mL) in a mixture 1:1 of THF/MeOH (15 mL), lithium hydroxide (7.553 mmol, 0.180 g) was added, and the reaction was stirred at RT overnight before distillation of volatiles. The residue was diluted with water, acidified with a solution of HCl (1N), and stirred for 1 hour. The formed precipitate was filtered off, and washed with water and petroleum ether to give 4-bromo-3-methoxy-benzoic acid. Yield: 56%.

Workup

  1. stirringstirred for 1 hour
  2. filtrationThe formed precipitate was filtered off
  3. washwashed with water and petroleum ether

Sources & evidence

ORD record
ord-f099e3a68e4741ac95b391142ccbd442
Source dataset
uspto-grants-2006_10
Patent number
US07122565B2

Reaction notes

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