Bromobenzene → 4-Methylbiphenyl

HRID 467247Notes

Reaction equation

HRID 467247 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4](S([O-])=O)=[CH:3][CH:2]=1.[Na+].Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O-2].[Ca+2]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:10][C:1]1[CH:6]=[CH:5][C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 7961BromobenzeneHCID 742671,2-Bis(diphenylphosphino)ethaneHCID 2723791Sodium p-toluenesulfinateHCID 6850728Calciumoxide

Product 1

HCID 125664-Methylbiphenyl

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

3.56 g (20 mmol) of sodium p-toluenesulfinate, 3.14 g (20 mmol) of bromobenzene, 0.0225 g (0.1 mmol) of palladium acetate, 0.0478 g (0.12 mmol) of 1,2-bis(diphenylphosphino)-ethane, 11.2 g (200 mmol) of calcium oxide and 60 ml of each solvent indicated in Table 1 were placed in a 100 ml round bottom flask and reacted at 150° C. in a nitrogen gas stream for 6 hours, respectively. After the completion of the reaction, the amount of 4-methyl-biphenyl formed was analyzed by means of high performance liquid chromatography. The results are shown in Table 1.

Workup

  1. customwere placed in a 100 ml round bottom flask
  2. customreacted at 150° C. in a nitrogen gas stream for 6 hours
  3. customAfter the completion of the reaction

Sources & evidence

ORD record
ord-bac4f20160394a60924409c075862d33
Source dataset
uspto-grants-1992_10
Patent number
US05159082

Reaction notes

Loading…