3-Hydroxy-2-naphthoic acid → 4-Bromo-3-hydroxy-2-naphthoic acid

HRID 1361005

Reaction equation

HRID 1361005 reaction equation
[OH:1][C:2]1[C:3]([C:12]([OH:14])=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Br:15]Br>C(O)(=O)C>[Br:15][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:12]([OH:14])=[O:13])[C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 71043-Hydroxy-2-naphthoic acidHCID 24408Bromine

Product 1

HCID 264194-Bromo-3-hydroxy-2-naphthoic acidYield 88.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

3-Hydroxynaphthalene-2-carboxylic acid (3.0 g, 15.9 mmol) was suspended in acetic acid (40 mL) and with vigorous stirring a solution of bromine (817 μL, 15.9 mmol) in acetic acid (10 mL) was added drop wise during 30 minutes. The suspension was stirred at room temperature for 1 hour, filtered and washed with water. Drying in vacuo afforded 3.74 g (88%) of 4-bromo-3-hydroxynaphthalene-2-carboxylic acid as a solid.

Workup

  1. additionwas added drop wise during 30 minutes
  2. filtrationfiltered
  3. washwashed with water
  4. customDrying in vacuo

Sources & evidence

ORD record
ord-cec279efa24d480ba329f30936792dee
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Linked notes

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