Toluene → p-Chlorophenyldimethylvinylsilane
Reaction equation
[CH3:1][Si:2]([CH3:5])(Cl)Cl.[C:6]1(C)[CH:11]=CC=C[CH:7]=1.[Cl:13][C:14]1[CH:19]=[CH:18]C([Mg]Cl)=[CH:16][CH:15]=1.C([Mg]Cl)=C>O1CCCC1>[Cl:13][C:14]1[CH:15]=[CH:16][C:1]([SiH2:2][CH:5]=[C:6]([CH3:11])[CH3:7])=[CH:18][CH:19]=1Participants
Procedure
Forty cubic centimeters (0.33 mol) of dimethyldichloro silane at 20° C. were placed in a 3-neck balloon-flask swept by a flow of nitrogen. Eighty cubic centimeters of toluene were added while shaking the mixture. The temperature was reduced to 5° C., then 0.33 mol of p-chlorophenylmagnesium chloride in 30 mn in the form of a solution in tetrahydrofurane (140 cubic centimeters) were added. Twenty cubic centimeters of toluene were added and the mixture was shaken for 2 hours 30 minutes. Then, 0.36 mol of vinylmagnesium chloride at 20 mn in the form of a solution in tetrahydrofurane (120 cubic centimeters) were added, the temperature being 25° C. at that time. Then the temperature of the reactive environment was changed and maintained for 2 hours. The reactive environment was cooled, the mixture was washed twice with 100 cubic centimeters of water, acidified with 5 cubic centimeters of HCl. Then, after decantation, the mixture was neutralized by means of sodium bicarbonate, dried, and 42 grams of a product containing (chromatography in the gaseous phase) 80 percent in terms of weight of p-chlorophenyldimethylvinylsilane (yield of 51.3 percent as compared to dimethylchlorosilane) was collected.
Workup
- customwas reduced to 5° C.
- stirringthe mixture was shaken for 2 hours 30 minutes
- custombeing 25° C. at that time
- temperaturemaintained for 2 hours
- temperatureThe reactive environment was cooled
- washthe mixture was washed twice with 100 cubic centimeters of water
- customdried
Sources & evidence
- ORD record
- ord-d17e7aa297d7450086d97ca2a1839b87
- Source dataset
- uspto-grants-1979_12
- Patent number
- US04180515
Reaction notes
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