Trifluoroacetic anhydride → 2-Cyano-4-nitrobiphenyl

HRID 743861Notes

Reaction equation

HRID 743861 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-4nitrobiphenyl. (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-d00223d48ea94eb8baaf3a6cf7024ee7
Source dataset
uspto-grants-1996_09
Patent number
US05556981

Reaction notes

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