1-Bromo-2-nitro-4-(trifluoromethoxy)benzene → 2-Nitro-4-(trifluoromethoxy)benzonitrile

HRID 430441Notes

Reaction equation

HRID 430441 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:6][C:5]=1Br)([O-:3])=[O:2].[Cu][C:17]#[N:18]>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:6][C:5]=1[C:17]#[N:18])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 183504491-Bromo-2-nitro-4-(trifluoromethoxy)benzeneHCID 178418546HCID 178418546, compound

Product 1

HCID 183504782-Nitro-4-(trifluoromethoxy)benzonitrileYield 68.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 2-nitro-4-trifluoromethoxy-bromobenzene (2.0 g) in N,N-dimetbylformamide (2 ml) was treated with copper (I) cyanide (0.62 g) and the mixture heated at 150° C. for 1 hour. Toluene (10 ml) was added and the mixture was maintained at reflux for 1 hour. The mixture was filtered and the filtrate evaporated to give a dark oil which was purified by chromatography eluting with ethyl acetate/hexane (1:9) to give 2-nitro-4-trifluoromethoxybenzonitrile (1.1 g) as a yellow liquid, NMR (CDCl3) 7.65(m,1H), 8.0(d,1H), 8.15(m,1H).

Workup

  1. temperaturethe mixture was maintained
  2. temperatureat reflux for 1 hour
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated
  5. customto give a dark oil which
  6. customwas purified by chromatography
  7. washeluting with ethyl acetate/hexane (1:9)

Sources & evidence

ORD record
ord-afd57895d27e4b7599014cdd159e0be9
Source dataset
uspto-grants-2001_11
Patent number
US06323155B1

Reaction notes

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