Trifluoroacetic anhydride → 2-Cyano-4-nitrobiphenyl

HRID 866228Notes

Reaction equation

HRID 866228 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 im 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 im vacuo

Sources & evidence

ORD record
ord-95f52842482945cda3edd2d0781cd1f3
Source dataset
uspto-grants-1996_10
Patent number
US05569768

Reaction notes

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