(1,1'-Biphenyl)-4-carbonitrile → 4'-(2-Bromoacetyl)[1,1'-biphenyl]-4-carbonitrile

HRID 2183433Notes

Reaction equation

HRID 2183433 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][CH2:6][C:7](Br)=[O:8].[C:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)#[N:11]>ClCCl>[Br:5][CH2:6][C:7]([C:21]1[CH:20]=[CH:19][C:18]([C:15]2[CH:14]=[CH:13][C:12]([C:10]#[N:11])=[CH:17][CH:16]=2)=[CH:23][CH:22]=1)=[O:8]

Participants

5

Reactant 3

HCID 18021(1,1'-Biphenyl)-4-carbonitrileHCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 224728864'-(2-Bromoacetyl)[1,1'-biphenyl]-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4.68 g aluminium chloride (35.15 mmol) are dissolved in 45 ml dichloromethane and treated dropwise with 3.38 g (16.74 mmol) bromoacetyl bromide at 0° C. After 30 min 3 g (16.74 mmol) 4-cyanobiphenyl, dissolved in 15 ml dichloromethane, are added dropwise. The reaction mixture is stirred overnight at ambient temperature, added to ice-water and extracted 2 times with dichloromethane. The organic phase is washed with water and brine, dried and evaporated. The residue is triturated with petrol ether, filtered and dried. Yield: 4.24 g (83%).

Workup

  1. additionare added dropwise
  2. extractionextracted 2 times with dichloromethane
  3. washThe organic phase is washed with water and brine
  4. customdried
  5. customevaporated
  6. customThe residue is triturated with petrol ether
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-f20646f5d90149d38ac02e2aff389e33
Source dataset
uspto-grants-2005_05
Patent number
US06900194B1

Reaction notes

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