Acetic Acid → 5-Bromonaphthalene-2-carboxylic acid

HRID 1590376Notes

Reaction equation

HRID 1590376 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[C:5](=[CH:7][CH:8]=[CH:9][C:10]=2C(O)=O)[CH:6]=1.II.[Br:16]Br.[C:18]([OH:21])(=[O:20])C>BrBr>[Br:16][C:10]1[CH:9]=[CH:8][CH:7]=[C:5]2[C:4]=1[CH:3]=[CH:2][C:1]([C:18]([OH:21])=[O:20])=[CH:6]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 807IodineHCID 68471-Naphthoic acidHCID 24408Bromine

Product 1

HCID 149606465-Bromonaphthalene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 24408BromineCatalyst

Procedure

To naphthoic acid (50 g) (ex Aldrich) in glacial acetic acid at reflux was added a few drops of bromine (ex BDH) followed by iodine (0.5 g) (ex (BDH). Bromine (15 ml) was added dropwise over one hour. The mixture was cooled to 25° and stirred there for 18 hours. The resulting white precipitate was filtered, dissolved in hot water and treated with concentrated hydrochloric acid. The precipitate was filtered and dried (over phosphorus pentoxide (ex BDH) to give 5-bromo-2-napthoic acid (recrystallised from ethanol) (28 g). Melting point 261°-2°. NMR 1H:(DMSO,CDCl3), 8.60(1H,s), 8.00(5H,m), 7.40(1H,m).

Workup

  1. temperatureThe mixture was cooled to 25°
  2. filtrationThe resulting white precipitate was filtered
  3. dissolutiondissolved in hot water
  4. additiontreated with concentrated hydrochloric acid
  5. filtrationThe precipitate was filtered
  6. dry with materialdried (over phosphorus pentoxide (ex BDH)

Sources & evidence

ORD record
ord-349a6dae78c1414ca5a23eea3348f7bb
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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