Dimethylformamide → 4-Chloro-2-nitrobenzonitrile

HRID 370635

Reaction equation

HRID 370635 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Cu][C:13]#[N:14].CN(C)C=O.C(OCC)(=O)C>>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:13]#[N:14])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 69772,5-DichloronitrobenzeneHCID 8857Ethyl AcetateHCID 178418546HCID 178418546, compound

Product 1

HCID 969244-Chloro-2-nitrobenzonitrileYield 63%

Procedure

A mixture of 7.7 g (0.040 mol) of 2,5-dichloronitrobenzene and 4.0 g (0.044 mol) of copper (I) cyanide in 4.0 ml (0.05 mol) of N,N-dimethylformamide was refluxed for 3.5 hours. The reaction mixture was poured slowly into 39 ml (0.40 mol) of ethyl acetate and followed by stirring for 10 hours at room temperature. The precipitate was filtered and washed with 3 ml of ethyl acetate. After concentration of the combined filtrate, the residue gave 4.6 g (63.0%) of 4-chloro-2-nitrobenzonitrile purified by the procedure of Example 1.

Workup

  1. temperaturewas refluxed for 3.5 hours
  2. filtrationThe precipitate was filtered
  3. washwashed with 3 ml of ethyl acetate

Sources & evidence

ORD record
ord-92feba178098441aa1eabb90f9bbe19e
Source dataset
uspto-grants-1985_07
Patent number
US04528143

Linked notes

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