Hydrochloric Acid → 2-Benzoyl-4-bromobenzoic acid

HRID 750114Notes

Reaction equation

HRID 750114 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[C:4]([C:9](=[O:10])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:11][CH:12]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 665904-Bromophthalic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3467342-Benzoyl-4-bromobenzoic acidYield 87.8%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromophthalic acid anhydride (100 g) in benzene (500 ml) was added aluminum chloride (118 g), and the mixture was stirred at room temperature for 1 hr. and subsequently refluxed for 30 min. After cooling the reaction mixture, it was diluted with ethyl acetate (200 ml) and poured into ice water. Conc. hydrochloric acid (50 ml) was added and the mixture was stirred at room temperature for 30 min. After separating the organic layer, the layer was washed successively with 4N hydrochloric acid, water and brine, dried over sodium sulfate and concentrated until crystals precipitated. The crude crystals were collected by filtration, and recrystallized from toluene/ethyl acetate (10:1) to give 4-bromo-2-benzoylbenzoic acid (59 g) as colorless crystals.

Workup

  1. temperatureand subsequently refluxed for 30 min
  2. temperatureAfter cooling the reaction mixture, it
  3. stirringthe mixture was stirred at room temperature for 30 min
  4. customAfter separating the organic layer
  5. washthe layer was washed successively with 4N hydrochloric acid, water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated until crystals
  8. customprecipitated
  9. filtrationThe crude crystals were collected by filtration
  10. customrecrystallized from toluene/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-55aa9cf336ee4b9d8e179d02f1a1c106
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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