1-Hydroxy-2-naphthoic acid → 4-Bromo-1-hydroxynaphthalene-2-carboxylic acid

HRID 335049

Reaction equation

HRID 335049 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([OH:14])=[O:13].[Br:15]Br>C(O)(=O)C>[Br:15][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([OH:1])=[C:3]([C:12]([OH:14])=[O:13])[CH:4]=1

Participants

4

Reactant 2

HCID 68441-Hydroxy-2-naphthoic acidHCID 24408Bromine

Product 1

HCID 2893934-Bromo-1-hydroxynaphthalene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1-hydroxy-2-naphthoic acid (10.2 g, 53.9 mmol) in 100 mL of acetic acid was added bromine (6.60 mL, 53.9 mmol) dropwise. After 72 hours, the reaction was filtered and the filter cake was washed with acetic acid (40 mL) and hexanes (150 mL) to provide 4-bromo-1-hydroxy-2-naphthoic acid that gave a proton NMR spectra consistent with theory.

Workup

  1. filtrationthe reaction was filtered
  2. washthe filter cake was washed with acetic acid (40 mL) and hexanes (150 mL)

Sources & evidence

ORD record
ord-da2eefd0dd944cde9cff264726e045a2
Source dataset
uspto-grants-2014_11
Patent number
US08883850B2

Linked notes

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