Sulfuric Acid → 2,5-Difluoro-4-nitroaniline

HRID 1030985

Reaction equation

CC1C=CC(S([NH:11][C:12]2[CH:17]=[C:16]([F:18])[C:15]([N+:19]([O-:21])=[O:20])=[CH:14][C:13]=2[F:22])(=O)=O)=CC=1.S(=O)(=O)(O)O.[OH-].[NH4+]>O>[F:22][C:13]1[CH:14]=[C:15]([N+:19]([O-:21])=[O:20])[C:16]([F:18])=[CH:17][C:12]=1[NH2:11]

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred mixture of 12.2 g (0.0370 mole) of N-(4-methylphenylsulfonyl)-2,5-difluoro-4-nitroaniline in 20 ml of water was added 70 ml of concentrated sulfuric acid. This mixture was heated at 90° C. for 15 minutes and then was allowed to cool and stir at room temperature for five days. The reaction mixture was poured into ice-water, and the aqueous mixture was neutralized with concentrated ammonium hydroxide. The resulting solid was collected by filtration. The filter cake was washed with water and was dried under reduced pressure to yield 6.15 g of 2,5-difluoro-4-nitroaniline. The nmr spectrum was consistent with the proposed structure.

Workup

temperatureto cool
filtrationThe resulting solid was collected by filtration
washThe filter cake was washed with water
customwas dried under reduced pressure

Sources & evidence

ORD record: ord-7d8468be17cf41d8a9b17fd06a33e3ff
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05108486

Linked notes

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