Ammonia → 4'-Formyl-biphenyl-4-carbonitrile

HRID 2254967Notes

Reaction equation

HRID 2254967 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Cu][C:17]#[N:18].N>CN(C)C=O>[C:17]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1)#[N:18]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 13928194'-Bromo-[1,1'-biphenyl]-4-carbaldehydeHCID 178418546HCID 178418546, compound

Product 1

HCID 27592144'-Formyl-biphenyl-4-carbonitrileYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

10.0 g of 4'-bromo-4-biphenylcarboxaldehyde and 5.31 g of copper(I) cyanide were dissolved in 80 ml of dimethylformamide while gassing with argon and the solution was heated to reflux for 15 hours at 180° C. bath temperature. Thereafter, the reaction mixture was poured cautiously into 200 ml of 25 percent ammonia and extracted three times with 200 ml of methylene chloride each time. The organic phases were washed once with 200 ml of 25 percent ammonia and twice with 200 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the yellowish, crystalline residue (8.7 g) on silica gel gave 5.85 g (74%) of 4'-cyano-4-biphenylcarboxaldehyde as slightly yellowish crystals; Rf-value (toluene/ethyl acetate vol. 90:10) 0.27.

Workup

  1. temperaturethe solution was heated
  2. extractionextracted three times with 200 ml of methylene chloride each time
  3. washThe organic phases were washed once with 200 ml of 25 percent ammonia and twice with 200 ml of water each time
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8a30e141cb144fe7ae675c51d6814816
Source dataset
uspto-grants-1993_08
Patent number
US05238602

Reaction notes

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