Iodine → 5-Bromonaphthalene-2-carboxylic acid

HRID 2221289Notes

Reaction equation

HRID 2221289 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=[O:12].[Br:14]Br.II>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][C:2]([C:11]([OH:13])=[O:12])=[CH:1]2

Participants

5

Reactant 3

HCID 807IodineHCID 71232-Naphthoic acidHCID 24408Bromine

Product 1

HCID 149606465-Bromonaphthalene-2-carboxylic acidYield 53.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a boiling solution of 2-naphthoic acid (10.00 g, 58.14 mmol) in acetic acid (50 mL) is added dropwise bromine (3 mL) containing iodine (0.25 g). After the addition is complete, the solution is refluxed for 0.5 hr. A white precipitate forms during cooling and is isolated by filtration, washed with acetic acid and then water. The solid is triturated in methanol (100 mL) and 7.01 g (53.4% yield) of the desired product is obtained as a white solid. m.p. 248-250° C. 1H NMR (300 MHz, CD3OD): δ 8.94 (d, J=1.8 Hz, 1H), 8.52-8.42 (m, 3H), 8.27 (dd, J=1.8, 7.5 Hz, 1H), 7.79 (t, J=8.4 Hz, 1H).

Workup

  1. additionAfter the addition
  2. temperaturethe solution is refluxed for 0.5 hr
  3. temperatureA white precipitate forms during cooling
  4. customis isolated by filtration
  5. washwashed with acetic acid
  6. customThe solid is triturated in methanol (100 mL)

Sources & evidence

ORD record
ord-49889830defc4e909a60fd35f4a4cc42
Source dataset
uspto-grants-2008_05
Patent number
US07368462B1

Reaction notes

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