Bromobenzene → 4-Methylbiphenyl

HRID 467248Notes

Reaction equation

HRID 467248 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.[O-2].[Ca+2]>CN1CCCC1=O>[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

5

Reactant 3

HCID 7961BromobenzeneHCID 2723791Sodium p-toluenesulfinateHCID 6850728Calciumoxide

Product 1

HCID 125664-Methylbiphenyl

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

3.56 g (20 mmol) of sodium p-toluenesulfinate, 3.14 g (20 mmol) of bromobenzene, 11.2 g (200 mmol) of calcium oxide, 60 ml of N-methyl-2-pyrrolidone and each catalyst compound and each organophosphorus compound ligand indicated in Table 2 were placed in 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-methylbiphenyl formed was analyzed by means of high performance liquid chromatography. The results are shown in Table 2.

Workup

  1. customwere placed in 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-846ff05833704dbd987410263f9c15f3
Source dataset
uspto-grants-1992_10
Patent number
US05159082

Reaction notes

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