Hydrochloric Acid → 4-Amino-2-bromo-5-fluorobenzoic acid

HRID 1807773Notes

Reaction equation

HRID 1807773 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([Br:13])[CH:3]=1.[OH-].[Li+].Cl>O1CCCC1.O>[NH2:1][C:2]1[C:11]([F:12])=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([Br:13])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67059665HCID 67059665, compound

Product 1

HCID 670596864-Amino-2-bromo-5-fluorobenzoic acidYield 89.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of the intermediate methyl 4-amino-2-bromo-5-fluorobenzoate (5.24 mmol, 1.3 g) in tetrahydrofuran (15 mL) was treated with a solution of lithium hydroxide (15.72 mmol, 0.66 g) in water (15 mL) and stirred at 60° C. for 4 hours. The reaction mixture was then cooled to room temperature, taken to ˜pH 5 with dilute hydrochloric acid and concentrated under vacuum. The residue was dissolved in tetrahydrofuran and purified by column chromatography (9:1 dichloromethane/methanol) to give the title compound (1.1 g). 1H NMR ((CD3)2SO, 400 MHz): δ6.11 (2H, s), 7.02 (1H, d), 7.52 (1H, d)

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in tetrahydrofuran
  4. custompurified by column chromatography (9:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-5e1d0713d8ae4bf797455065963261ca
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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