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

HRID 1275002

Reaction equation

HRID 1275002 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 acidYield 76.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred suspension of 1-naphthoic acid (90 g, 0.52 mol) in glacial acetic acid at 100° C. was added bromine (84 g, 0.52 mol). The reaction was stirred at this temperature for 1.5 hours and then allowed to cool overnight. The resulting slurry was diluted with glacial acetic acid, the solid collected by filtration, resuspended in water, filtered and dried in vacuo to give 5-bromo-1-napthoic acid (100 g). The acid was converted to the title compound using a similar procedure to Description 3 (68%).

Workup

  1. temperatureto cool overnight
  2. filtrationthe solid collected by filtration
  3. filtrationfiltered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-e9e92af35b7048118ae5132f21b707db
Source dataset
uspto-grants-2000_12
Patent number
US06159979

Linked notes

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