Nitric Acid → 6-Fluoro-3-nitro-2-trifluoromethyl-benzoic acid

HRID 2293610

Reaction equation

[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[F:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[C:12]=1[C:13]([OH:15])=[O:14].O>ClCCl>[F:10][C:11]1[C:12]([C:13]([OH:15])=[O:14])=[C:16]([C:20]([F:21])([F:22])[F:23])[C:17]([N+:1]([O-:4])=[O:2])=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1.05 ml (23.3 mmol) of concentrated nitric acid (65%), which also was precooled to 0° C., is instilled in a solution of 17.5 ml of concentrated sulfuric acid and 2.5 g (12.0 mmol) of 2-fluoro-6-trifluoromethyl-benzoic acid, cooled to 0° C. It is allowed to stir for one more hour at 0° C. and then overnight at room temperature. It is then poured in a mixture of ice, water and dichloromethane, the organic phase is separated and the aqueous phase is extracted with dichloromethane. The organic solutions are combined, washed with saturated sodium chloride solution, dried on sodium sulfate and evaporated to dryness in a vacuum. The title compound is obtained in crystalline form.

Workup

customalso was precooled to 0° C.
customovernight
customat room temperature
customthe organic phase is separated
extractionthe aqueous phase is extracted with dichloromethane
washwashed with saturated sodium chloride solution
customdried on sodium sulfate
customevaporated to dryness in a vacuum

Sources & evidence

ORD record: ord-62788c37a7ea49d1ad1694bc8f5df3e4
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05686492

Linked notes

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