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

HRID 2042916Notes

Reaction equation

HRID 2042916 reaction equation
[Br:1]Br.[OH:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[C:14]([OH:16])=[O:15]>C(O)(=O)C>[Br:1][C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([OH:3])=[C:5]([C:14]([OH:16])=[O:15])[CH:6]=1

Participants

4

Reactant 2

HCID 68441-Hydroxy-2-naphthoic acidHCID 24408Bromine

Product 1

HCID 2893934-Bromo-1-hydroxynaphthalene-2-carboxylic acidYield 92.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (6.1 mL, 120 mmol) was added to a solution of naphthoic acid 17 (18.9 g, 100 mmol) in glacial acetic acid (250 mL). The mixture was stirred at room temperature overnight. The resulting solid was filtered and dried in vacuo to provide the titled compound 18 (24.7 g, 92%) as a white solid.

Workup

  1. filtrationThe resulting solid was filtered
  2. customdried in vacuo

Sources & evidence

ORD record
ord-41d693948ca74c9899da0024e5940776
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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