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

HRID 2360393
Notes
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Reaction equation

HRID 2360393 reaction equation
[F:1][C:2]([C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:12]=1)([C:7]([F:10])([F:9])[F:8])[C:3]([F:6])([F:5])[F:4].CN(C=O)C.[Br:27]N1C(=O)CCC1=O>O>[Br:27][C:16]1[CH:17]=[C:11]([C:2]([F:1])([C:3]([F:6])([F:5])[F:4])[C:7]([F:10])([F:9])[F:8])[CH:12]=[C:13]([C:18]([F:19])([F:20])[F:21])[C:14]=1[NH2:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 582974594-[1,2,2,2-Tetrafluoro-1-(trifluoromethyl)ethyl]-2-(trifluoromethyl)benzenamine

Product 1

HCID 582975582-Bromo-4-(1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl)-6-(trifluoromethyl)benzenamineYield 80%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
60 °C

Procedure

100 g (0.273 mol) of 4-(heptafluoropropan-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

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

Sources & evidence

ORD record
ord-c4b2b6eb60eb492eb0e30e5c10d1351a
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08686044B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes