Lithium Hydroxide → 4-Bromo-3-methoxybenzoic acid

HRID 1051848Notes

Reaction equation

HRID 1051848 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[O:12][CH3:13].[OH-].[Li+]>C1COCC1.CO.O>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:12][CH3:13]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 14570117Methyl 4-bromo-3-methoxybenzoate

Product 1

HCID 162158674-Bromo-3-methoxybenzoic acidYield 95.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 4-bromo-3-methoxybenzoate (11.2 g) in THF (130 mL), methanol (45 mL) and water (45 mL) was added a 1 M solution of lithium hydroxide in water (140 mL). The mixture was stirred at room temperature for 1 h. The solvent was removed in vacuum. Water was added and 1 N hydrochloric acid was added with ice bath cooling until pH 4 was reached. The precipitated solid was collected by filtration, washed with water and dried in vacuum to give 10.1 g of the title compound, that was used without further purification.

Workup

  1. customThe solvent was removed in vacuum
  2. additionWater was added
  3. addition1 N hydrochloric acid was added with ice bath
  4. temperaturecooling until pH 4
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed with water
  7. customdried in vacuum

Sources & evidence

ORD record
ord-21e557b5e3d24a958986f0a2d76de243
Source dataset
uspto-grants-2016_07
Patent number
US09388177B2

Reaction notes

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