Hydrochloric Acid → 4-(4-Iodophenyl)benzonitrile

HRID 2372978

Reaction equation

HRID 2372978 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Hg](C#N)[C:16]#[N:17].N1C=CC=CC=1.Cl>CN(C)C=O>[I:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:16]#[N:17])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 11591Mercuric cyanideHCID 763484,4'-Diiodo-1,1'-biphenyl

Product 1

HCID 13930054-(4-Iodophenyl)benzonitrileYield 86.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 15 g (33.2.10-3 mol) of 4,4'-diiodo-1,1'-biphenyl, 3.13 g (34.9.10-3 mol) of mercuric cyanide and 2.75 g (34.9.10-3 mol) of pyridine is heated at 200° C. for 15 minutes and 6 ml of dimethylformamide are then added to the mixture. After cooling, the reaction medium is hydrolyzed with a 1N aqueous solution of hydrochloric acid. The expected product is extracted with ethyl acetate. The organic phase obtained is washed with water until the pH of the washings is neutral, dried over magnesium sulfate and evaporated under vacuum. 3.28 g (yield: 33%) of a yellow solid are obtained after purification by flash chromatography using a chloroform/toluene mixture (1/1 v/v) as the eluent.

Workup

  1. temperatureAfter cooling
  2. extractionThe expected product is extracted with ethyl acetate
  3. customThe organic phase obtained
  4. washis washed with water until the pH of the washings
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-416499616194444f888a6cad8972cf0f
Source dataset
uspto-grants-1992_03
Patent number
US05101048

Linked notes

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