(4-Chloro-phenyl)-(4,5-difluoro-2-iodo-phenyl)-diazene → 2-(4-Chloro-phenylazo)-4,5-difluoro-benzonitrile

HRID 1690537Notes

Reaction equation

HRID 1690537 reaction equation
[Cu][C:2]#[N:3].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]=[N:12][C:13]2[CH:18]=[C:17]([F:19])[C:16]([F:20])=[CH:15][C:14]=2I)=[CH:7][CH:6]=1>C(O)CC.C(Cl)Cl.CCCCCCC>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]=[N:12][C:13]2[CH:18]=[C:17]([F:19])[C:16]([F:20])=[CH:15][C:14]=2[C:2]#[N:3])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 86640263(4-Chloro-phenyl)-(4,5-difluoro-2-iodo-phenyl)-diazeneHCID 178418546HCID 178418546, compound

Product 1

HCID 866402642-(4-Chloro-phenylazo)-4,5-difluoro-benzonitrileYield 77%

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 21907733Dichloromethane heptaneSolvent

Procedure

Copper (I) cyanide (9.76 g, 109 mmol) was added to a solution of (4-chloro-phenyl)-(4,5-difluoro-2-iodo-phenyl)-diazene (5.89 g, 16 mmol) in 1-propanol (95 ml) under an argon atmosphere. The reaction mixture was heated under reflux conditions for 14 h and diluted with CH2Cl2/heptane 1/1 (70 ml). The suspension was filtered and the filtrate was evaporated to dryness to give the title compound (3.3 g, 12 mmol; 77%) as brown solid which was used in the next step without further purification. MS: m/e=278.0 [M+H+].

Workup

  1. temperatureThe reaction mixture was heated under reflux conditions for 14 h
  2. filtrationThe suspension was filtered
  3. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-986fb914bb724082b587f5dcada527b3
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

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