Hydrochloric Acid → 3'-Bromo-4'-methyl-1,1'-biphenyl-2-carbonitrile

HRID 1739085Notes

Reaction equation

HRID 1739085 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:13]([C:18]#[N:19])=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:8][CH:7]=1.[Br:20]Br.Cl>ClCC(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[Br:20][C:11]1[CH:10]=[C:9]([C:12]2[C:13]([C:18]#[N:19])=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:8]=[CH:7][C:6]=1[CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24408BromineHCID 1455122-Cyano-4'-methylbiphenylHCID 6451240Aluminum(III) Chloride3×

Product 1

HCID 218403383'-Bromo-4'-methyl-1,1'-biphenyl-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 124181,1,1,2-TetrachloroethaneSolvent2×

Procedure

A suspension of 21.0 g (0.157 mol) of anhydrous aluminium chloride in 800 ml of tetrachloroethane is treated with 25.0 g (0.129 mol) of 4'-methyl-1,1'-biphenyl-2-carbonitrile and brought to an internal temperature of 60° with stirning. As soon as the aluminium chloride has gone into solution, a solution of 20.7 g (0.129 mol) of bromine in 100 ml of tetrachloroethane is added dropwise at an internal temperature of 60°. The reaction mixture is stirred at 60° for 24 hours. After addition of a further 6.2 g of aluminium chloride and warming to 60-70°, starting material can no longer be detected in the TLC (toluene). The reaction mixture is then decomposed with 20 ml of conc. hydrochloric acid with ice-cooling, and the organic phase is separated off and evaporated in vacuo. The dark residue is dissolved in ethyl acetate, washed with water and sodium carbonate solution, dried (MgSO4) and evaporated. The crude product is purified by flash chromatography, as a result of which 22.0 g (62% of theory) of the title compound are obtained, m.p. 104-106° (from cyclohexane).

Workup

  1. custombrought to an internal temperature of 60° with stirning
  2. temperaturewarming to 60-70°
  3. temperaturecooling
  4. customthe organic phase is separated off
  5. customevaporated in vacuo
  6. dissolutionThe dark residue is dissolved in ethyl acetate
  7. washwashed with water and sodium carbonate solution
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe crude product is purified by flash chromatography

Sources & evidence

ORD record
ord-cf8d5d88e3d24569931e4e4c68fd0a15
Source dataset
uspto-grants-1999_10
Patent number
US05965592

Reaction notes

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