Benzyl Bromide → (3-Vinylphenyl)phenylmethane
Reaction equation
[Na].[Mg].[Br-].[CH:4]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[CH2:5].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCCC1.CCOCC.Cl[Ni]Cl.O>[CH:4]([C:6]1[CH:11]=[C:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=[CH:8][CH:7]=1)=[CH2:5]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 80 °C
Procedure
To a 2 liter three-neck flask equipped with a reflux condenser and a stirrer was added 50 ml of tetrahydrofuran which was dried with metallic sodium and 28 g (1.15 mole) of metallic magnesium and it was maintained with starring at room temperature. Then, a solution of 183 g (1.02 mole) of 3-vinylbenzene bromide in 500 ml of dry tetrahydrofuran was added dropwise over 2 hours to the above contents. The reaction temperature was maintained at 80° C. After the dropping of the solution, the stirring was continued for further 1 hour at 80° C. The thus obtained Grignard reagent solution was added dropwise over 2 hours to the solution of 171 g (1.0 mole) of benzyl bromide and 5.5 g of NiCl2 (Ph2P(CH)3PPh2) in 500 ml of dry ether Stirring was continued for further 1 hour at 35° C. This reaction mixture was poured into iced water and an oily layer was separated. Ether and tetrahydrofuran were evaporated off under reduced pressure to obtain (3-vinylphenyl)phenylmethane of the formula (I) in a yield of 60%.
Workup
- customTo a 2 liter three-neck flask equipped with a reflux condenser and a stirrer
- temperaturewas maintained
- customwith starring at room temperature
- waitwas continued for further 1 hour at 35° C
- customan oily layer was separated
- customEther and tetrahydrofuran were evaporated off under reduced pressure
Sources & evidence
- ORD record
- ord-a91c518f047443208727efe1dcad8865
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04922052
Reaction notes
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