2-Benzoylbenzoic Acid → 3-Phenyl-3-(5-bromo-1-benzotriazolyl)phthalide

HRID 615669Notes

Reaction equation

HRID 615669 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:18][C:19]1[CH:27]=[CH:26][C:22]2[NH:23][N:24]=[N:25][C:21]=2[CH:20]=1>C1(C)C(C)=CC=CC=1>[C:2]1([C:1]2([N:23]3[C:22]4[CH:26]=[CH:27][C:19]([Br:18])=[CH:20][C:21]=4[N:25]=[N:24]3)[C:9]3[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:11](=[O:13])[O:8]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 68132-Benzoylbenzoic AcidHCID 178419334HCID 178419334, compound

Product 1

HCID 204268393-Phenyl-3-(5-bromo-1-benzotriazolyl)phthalide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

10.0 g (0.04 mol.) of commercial 2-benzoylbenzoic acid and 7.8 g (0.04 mol.) of 5-bromobenzotriazole were added to 300 ml of dried xylene, and refluxed for 8 hours as heat was applied thereto by means of the dehydration-reflexing apparatus. After cooling, the insoluble material was filtered off with suction, and the filtrate was concentrated to obtain 12.4 g of oily substance. This oily substance was separated and purified by flash column chromatography (silica gel: 400 g, eluate: hexane-ethyl acetate (3:2 by volume) mixture) to obtain the intended compound, 3-phenyl-3-(5-bromo-1-benzotriazolyl)phthalide (22), in the form of white crystals. Yield 8.1 g, Melting Point 128° to 131° C.

Workup

  1. temperaturerefluxed for 8 hours
  2. temperatureas heat
  3. temperatureAfter cooling
  4. filtrationthe insoluble material was filtered off with suction
  5. concentrationthe filtrate was concentrated
  6. customto obtain 12.4 g of oily substance
  7. customThis oily substance was separated
  8. custompurified by flash column chromatography (silica gel: 400 g, eluate: hexane-ethyl acetate (3:2 by volume) mixture)

Sources & evidence

ORD record
ord-8af61a665b9b439f80a7f69b34635963
Source dataset
uspto-grants-1985_02
Patent number
US04500636

Reaction notes

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