Lithium Hydroxide → 3-Bromo-5-fluoro-4-methoxybenzoic acid

HRID 521536Notes

Reaction equation

HRID 521536 reaction equation
C[O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([O:11][CH3:12])=[C:6]([Br:13])[CH:5]=1.[OH-].[Li+]>C1COCC1.O>[Br:13][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([F:10])[C:7]=1[O:11][CH3:12])[C:3]([OH:14])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67076673Methyl 3-bromo-5-fluoro-4-methoxybenzoate

Product 1

HCID 118070333-Bromo-5-fluoro-4-methoxybenzoic acidYield 52.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5.8 g of the product obtained in step 2 were dissolved in 100 ml of a mixture of THF and water (9:1), 1.06 g (44.1 mmol) of lithium hydroxide were added and the mixture was stirred for 3 days. The solvent was evaporated and the residue was purified by preparative RP HPLC (water/ACN gradient). 2.9 g of the title compound were obtained.

Workup

  1. additionwere added
  2. customThe solvent was evaporated
  3. customthe residue was purified by preparative RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-d31e83c6bfd441a7b3b90f4fb51053a9
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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