Toluene → p-Chlorophenyldimethylvinylsilane

HRID 444312Notes

Reaction equation

HRID 444312 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]=1

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 6398DichlorodimethylsilaneHCID 178461836HCID 178461836, compoundHCID 178478983HCID 178478983, compound

Product 1

HCID 131711671p-ChlorophenyldimethylvinylsilaneYield 51.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

Forty cubic centimeters (0.33 mol) of dimethyldichlorosilane at 20° C. were placed in a three-neck balloon-flask swept by a flow of nitrogen. Eighty cubic centimeters of toluene were added while agitating the mixture. The temperature was changed to 5° C., then 0.33 mol of p-chiorophenylmagnesium chloride was added in 30 mn in the form of a solution in tetrahydrofurane (140 cubic centimeters). Twenty cubic centimeters of toluene were added and shaken for 2 hours 30 minutes. Then 0.36 mol of vinylmagnesium chloride was added in 20 mn in the form of a solution in tetrahydrofurane (120 cubic centimeters), with the temperature being maintained at 25° C. Then the temperature of the reactive environment was raised to 80° C. and maintained at that temperature for 2 hours. The reactive environment was cooled, the product was washed twice in 120 cubic centimeters of water acidified by 5 cubic centimeters of HCl. Then, after decantation, neutralization by means of bicarbonate of soda, drying, 42 grams of a product was collected containing (chromatography in gaseous phase) 80 percent by weight of p-chlorophenyldimethylvinylsilane (yield 51.3 percent as compared to dimethylchlorosilane.)

Workup

  1. customwas changed to 5° C.
  2. stirringshaken for 2 hours 30 minutes
  3. temperatureThen the temperature of the reactive environment was raised to 80° C.
  4. temperaturemaintained at that temperature for 2 hours
  5. temperatureThe reactive environment was cooled
  6. washthe product was washed twice in 120 cubic centimeters of water
  7. dry with materialThen, after decantation, neutralization by means of bicarbonate of soda, drying
  8. custom42 grams of a product was collected

Sources & evidence

ORD record
ord-c22ea725f80045fc82213afbbcb12360
Source dataset
uspto-grants-1981_04
Patent number
US04263436

Reaction notes

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