1-Naphthoic acid → 5-Bromonaphthalene-1-carboxylic acid

HRID 1505261Notes

Reaction equation

HRID 1505261 reaction equation
[C:1]1([C:11]([OH:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Br:14]Br>C(O)(=O)C>[Br:14][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][CH:2]=[C:1]2[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 68471-Naphthoic acidHCID 24408Bromine

Product 1

HCID 6976055-Bromonaphthalene-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1-naphtoic acid (commercially available) (15 g) in acetic acid (37 ml) was added dropwise bromine (4.5 ml). The reaction mixture was heated at reflux for 4 hours. The reaction mixture was then cooled to ambient temperature and stored at ambient temperature for 16 hours. The solids were isolated by filtration and washed with acetic acid and then ethanol to give 5-bromo-1-naphtoic acid (10.8 g) as a white solid. 1H-NMR (DMSO, 400 MHz): 8.85 (d, 1H), 8.40 (d, 1H), 8.21 (d, 1H), 7.98 (d, 1H), 7.76 (m, 1H), 7.55 (m, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 hours
  3. customThe solids were isolated by filtration
  4. washwashed with acetic acid

Sources & evidence

ORD record
ord-29c6d117241445e7884d9f7a234087d7
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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