Potassium Nitrate → 5-Bromo-4-chloro-3-nitroisatoic anhydride

HRID 1910231

Reaction equation

[Br:1][C:2]1[CH:13]=[C:6]2[C:7]([O:9][C:10](=[O:12])[NH:11][C:5]2=[CH:4][C:3]=1[Cl:14])=[O:8].[N+:15]([O-])([O-:17])=[O:16].[K+]>OS(O)(=O)=O>[Br:1][C:2]1[CH:13]=[C:6]2[C:7]([O:9][C:10](=[O:12])[NH:11][C:5]2=[C:4]([N+:15]([O-:17])=[O:16])[C:3]=1[Cl:14])=[O:8]

Participants

Conditions

Temperature: -20 °C

Procedure

5.4 g (20 mmol) of 5-bromo-4-chloroisatoic anhydride was suspended in 20 ml of conc. H2SO4 at −10° C. and cooled to −20° C. 2.1 g (21 mmol) of potassium nitrate was dissolved in 6 mL of sulfuric acid and cooled to 0° C., was then added dropwise to the reaction mixture. The reaction mixture was then stirred −10° C. for 15 min and warmed to room temperature overnight. The mixture was poured in to a beaker containing ice. The resulting solid was collected by filtration, washed with cold water and dried to produce 3.2 g (50%) of 5-bromo-4-chloro-3-nitroisatoic anhydride. LCMS: 323 (M+1)+.

Workup

temperaturecooled to 0° C.
additionwas then added dropwise to the reaction mixture
temperaturewarmed to room temperature overnight
additionThe mixture was poured in to a beaker
additioncontaining ice
filtrationThe resulting solid was collected by filtration
washwashed with cold water
customdried

Sources & evidence

ORD record: ord-91eb5a61040b419babf7808dcedf6f7c
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598353B2

Linked notes

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