Water → 2,2'-Bis(trifluoromethyl)-4,4'-dinitrobiphenyl

HRID 745141

Reaction equation

HRID 745141 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[OH2:15]>CN(C)C=O.[Cu]>[F:12][C:11]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:9])=[O:15])=[CH:4][C:3]=1[C:11]([F:12])([F:14])[F:13]

Participants

5

Reactant 2

HCID 962WaterHCID 1361982-Bromo-5-nitrobenzotrifluoride

Product 1

HCID 113724052,2'-Bis(trifluoromethyl)-4,4'-dinitrobiphenylYield 71%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

Activated copper (45 g) was added to a solution of 2-bromo-5-nitro-benzotrifluoride (50 g) in 100 ml of dimethylformamide and the mixture refluxed for 5 hours. The cooled mixture was poured into excess water and the resulting brown precipitate collected by filtration, washed with water and dried. Chromatography over silica gel gave 25 g (71% yield) of ##STR6## 2,2'-bis(trifluoromethyl)-4,4'-dinitro-1,1'-biphenyl, recrystallized as shiny yellow prisms from ether, m.p. 138°-140° C.

Workup

  1. temperaturethe mixture refluxed for 5 hours
  2. filtrationthe resulting brown precipitate collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-b44de8c1673540f19cbc8f51efc90023
Source dataset
uspto-grants-1986_07
Patent number
US04597891

Linked notes

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