Dimethylformamide → 2-Bromo-4-(1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl)-6-(trifluoromethyl)benzenamine

HRID 590906Notes

Reaction equation

[F:1][C:2]([F:21])([F:20])[C:3]([F:19])([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:9]=1)[C:4]([F:7])([F:6])[F:5].CN(C=O)C.[Br:27]N1C(=O)CCC1=O>O>[Br:27][C:13]1[CH:14]=[C:8]([C:3]([F:19])([C:4]([F:7])([F:6])[F:5])[C:2]([F:20])([F:21])[F:1])[CH:9]=[C:10]([C:15]([F:16])([F:17])[F:18])[C:11]=1[NH2:12]

Participants

Conditions

Temperature: 60 °C

Procedure

100 g (0.273 mol) of 4-(perfluoropropan-2-yl)-2-(trifluoromethyl)aniline was charged to 500 ml of DMF, and 52.1 g (0.287 mol) of N-bromosuccinimide was charged in separate portions thereto over 30 minutes. After stirring at 60° C. for 2 hours, and then cooling to room temperature, the mixture was discharged to 2000 ml of water. The mixture was extracted with ethyl acetate, then washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=20:1) to prepare 89.0 g (yield 80%) of a target compound.

Workup

additionwas charged in separate portions
temperaturecooling to room temperature
extractionThe mixture was extracted with ethyl acetate
washwashed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=20:1)

Sources & evidence

ORD record: ord-24427a633b744c05adf90649d15b78ae
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09237745B2

Reaction notes

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