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

HRID 1938858Notes

Reaction equation

HRID 1938858 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[C:18]([F:30])=[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:28]=[C:21]([C:22]([O:24][CH:25]([CH3:26])[CH3:27])=[O:23])[C:20]([Cl:29])=[CH:19][C:18]=2[F:30])=[O:9])[C:6]=1[C:11]([OH:10])=[O:12]

Participants

4

Reactant 2

HCID 12443Tetrabromophthalic anhydrideHCID 13519894Propan-2-yl 5-amino-2-chloro-4-fluorobenzoate

Product 1

HCID 5073152,3,4,5-Tetrabromo-6-[(4-chloro-2-fluoro-5-isopropoxycarbonyl-phenyl)carbamoyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Tetrabromophthalic anhydride (6.67 g, 0.014 mole) and 1-methylethyl 5-amino-2-chloro-4-fluorobenzoate (3.33 g, 0.014 mole) were heated to reflux with stirring in about 150 ml of toluene, then left overnight at room temperature. Filtration of the reaction mixture gave the title compound, m.p. 160°-165° C. (decomp.).

Workup

  1. temperatureto reflux
  2. filtrationFiltration of the reaction mixture

Sources & evidence

ORD record
ord-e3dd39b6e2654b0a98d17a918d348e25
Source dataset
uspto-grants-1997_12
Patent number
US05693827

Reaction notes

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