Hydrochloric Acid → Methyldiisopropylchlorosilane

HRID 846339Notes

Reaction equation

HRID 846339 reaction equation
[CH3:1][SiH:2]([CH:6]([CH3:8])[CH3:7])[CH:3]([CH3:5])[CH3:4].S(Cl)([Cl:12])(=O)=O.Cl.S(=O)=O>>[CH3:1][Si:2]([CH:6]([CH3:8])[CH3:7])([CH:3]([CH3:5])[CH3:4])[Cl:12]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 24648Sulfuryl chlorideHCID 101621268Diisopropyl(methyl)silane

Product 1

HCID 6421633Methyldiisopropylchlorosilane

Procedure

73 g (3.0 mol) magnesium was introduced into a 2 L four-neck flask equipped with a reflux condenser, stirring rod, thermometer, and addition funnel, and was dried under nitrogen. 1,000 mL dry THF was then added. A Grignard reagent was prepared by slowly dripping in 235.6 g (3.0 mol) isopropyl chloride from the addition funnel. 166.8 g (1.45 mol) methyldichlorosilane was then dripped in from the addition funnel. After completion of this addition, the reaction was brought to completion by continuing to stir for 2 hours at the reflux temperature of THF, followed by the addition of 350 mL water, with cooling, for hydrolysis. The reaction solution was recovered by decantation, and the THF was distilled out through a 30 cm Widmer precision distillation column. Continuing with distillation at ambient pressure afforded 160 g (1.2 mol) methyldiisopropylsilane (bp= 122 degrees Centigrade). 26.1 g (0.2 mol) of the methyldiisopropylsilane thus obtained was placed in a 50 mL three-neck flask equipped with a reflux condenser, thermometer, and addition funnel. 27 g (0.2 mol) sulfuryl chloride was carefully dripped in at 60 degrees Centigrade while stirring with a magnetic stirring bar. An exothermic reaction developed with the production of hydrogen chloride and sulfur dioxide. After addition of the entire quantity, the reaction was maintained for 1 hour at 70 degrees Centigrade and then distilled in vacuo. 27 g (0.16 mol) of the target methyldiisopropylchlorosilane (bp=64 degrees Centigrade32 mmHg) was obtained.

Workup

  1. customwas placed in a 50 mL three-neck flask
  2. customequipped with a reflux condenser
  3. additionthermometer, and addition funnel
  4. customwas carefully dripped in at 60 degrees Centigrade
  5. customAn exothermic reaction
  6. additionAfter addition of the entire quantity
  7. temperaturethe reaction was maintained for 1 hour at 70 degrees Centigrade
  8. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-23f692eaf58e4c3ca63c10d9d207edb5
Source dataset
uspto-grants-1992_08
Patent number
US05136074

Reaction notes

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