4-Bromophthalic anhydride → 2-Benzoyl-4-bromobenzoic acid

HRID 1797496Notes

Reaction equation

HRID 1797496 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-]>C1C=CC=CC=1>[C:9]([C:4]1[CH:3]=[C:2]([Br:1])[CH:12]=[CH:11][C:5]=1[C:6]([OH:8])=[O:7])(=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 665904-Bromophthalic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3467342-Benzoyl-4-bromobenzoic acidYield 98.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 4-bromophthalic anhydride (50 g, 220 mmol) in benzene (500 mL) was added aluminum chloride (60 g, 450 mmol) by small portions under ice-cooling. The obtained mixture was stirred at room temperature for 24 h. The reaction mixture was poured into ice water and extracted with a mixed solvent of ethyl acetate-tetrahydrofuran (1/1). The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography and recrystallized from ethyl acetate-diisopropyl ether. The precipitated crystals were collected by filtration to give 2-benzoyl-4-bromobenzoic acid (33 g, 49%)as crystals.

Workup

  1. temperaturecooling
  2. extractionextracted with a mixed solvent of ethyl acetate-tetrahydrofuran (1/1)
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. customrecrystallized from ethyl acetate-diisopropyl ether
  8. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-28ec2f3ff4d9469088cff57b7b418c23
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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