Tetrabromophthalic anhydride → 2,3,4,5-Tetrabromo-6-[(4-chloro-3-isopropoxycarbonyl-phenyl)carbamoyl]benzoic acid

HRID 326342

Reaction equation

HRID 326342 reaction equation
[Br:1][C:2]1[C:3]([Br:15])=[C:4]([Br:14])[C:5]([Br:13])=[C:6]2[C:11](=[O:12])[O:10][C:8](=[O:9])[C:7]=12.[NH2:16][C:17]1[CH:18]=[CH:19][C:20]([Cl:29])=[C:21]([CH:28]=1)[C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23]>C1(C)C=CC=CC=1>[Br:13][C:5]1[C:4]([Br:14])=[C:3]([Br:15])[C:2]([Br:1])=[C:7]([C:8]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([Cl:29])=[C:21]([C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH:28]=2)=[O:9])[C:6]=1[C:11]([OH:10])=[O:12]

Participants

4

Reactant 2

HCID 12443Tetrabromophthalic anhydrideHCID 369590Isopropyl 5-amino-2-chlorobenzoate

Product 1

HCID 5073162,3,4,5-Tetrabromo-6-[(4-chloro-3-isopropoxycarbonyl-phenyl)carbamoyl]benzoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Tetrabromophthalic anhydride (7.03 g, 0.015 mole), 1-methylethyl 5-amino-2-chlorobenzoate (3.24 g, 0.015 mole) and toluene (about 150 ml) were heated almost to reflux over 30 minutes. The reaction mixture was cooled and filtered to give the title compound, m.p. 169°-171° C. (decomp.) (8.92 g, 87% yield).

Workup

  1. temperatureto reflux over 30 minutes
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-28d9383bf766479eb480eb2c911469f3
Source dataset
uspto-grants-1993_12
Patent number
US05268389

Linked notes

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