Trifluoroacetic anhydride → 2-Cyano-4-nitrobiphenyl

HRID 976556Notes

Reaction equation

HRID 976556 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)#[N:2].[N+:15]([O-])([O-:17])=[O:16].[NH4+].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)(Cl)Cl>[C:1]([C:3]1[CH:8]=[C:7]([N+:15]([O-:17])=[O:16])[CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)#[N:2]

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 22985Ammonium nitrate2×HCID 141162(1,1'-Biphenyl)-2-carbonitrile

Product 1

HCID 214689572-Cyano-4-nitrobiphenylYield 94.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Cyanobiphenyl (0.111 moles, 20.0 g) and ammonium nitrate (10.0 grams) were added to 250 ml chloroform. Trifluoroacetic anhydride (80 ml) was added. The reaction mixture was stirred until the ammonium nitrate was dissolved. The reaction mixture was added to 300 ml of ice water. The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo to yield 23.5 g of 2-Cyano-4-nitrobiphenyl. (MS)

Workup

  1. dissolutionwas dissolved
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-289cc3603f384c688a4e5d086f0350f0
Source dataset
uspto-grants-1997_03
Patent number
US05612360

Reaction notes

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