Dichlorodiphenylsilane → tert-Butyldiphenylchlorosilane

HRID 974386Notes

Reaction equation

HRID 974386 reaction equation
[Mg].O1CCCC1.[C:7](Cl)([CH3:10])([CH3:9])[CH3:8].[C:12]1([Si:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(Cl)[Cl:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[Cu](C#N)C#N.CCCCCC>[C:7]([Si:18]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[Cl:19])([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 6627DichlorodiphenylsilaneHCID 8028TetrahydrofuranHCID 10486tert-BUTYL CHLORIDEHCID 5462224Magnesium

Product 1

HCID 94078tert-ButyldiphenylchlorosilaneYield 75%

Reagents, catalysts & solvents 2

HCID 178418260HCID 178418260, compoundCatalystHCID 8058HexaneSolvent

Procedure

12.2 g (0.5 mol) magnesium was introduced into a 500 mL four-neck flask equipped with a reflux condenser, addition funnel, thermometer, and stirring rod. After drying under a nitrogen atmosphere, the tert-butyl Grignard reagent was prepared by the addition of 250 mL tetrahydrofuran and 46.3 g (0.5 mol) t-butyl chloride with stirring. To this was added 0.45 g (0.005 mol) copper cyanide at room temperature, and 126.6 g (0.5 mol) diphenyldichlorosilane was then dripped in while stirring. The system temperature rose to 50 degrees Centigrade. After heating and stirring under reflux for 5 hours, the addition of 100 mL hexane, filtration, distillation of the solvent, and continuing with distillation in vacuo gave 103 g (yield =75%) tert-butyldiphenylchlorosilane.

Workup

  1. customequipped with a reflux condenser, addition funnel
  2. customAfter drying under a nitrogen atmosphere
  3. stirringwith stirring
  4. stirringwhile stirring
  5. customrose to 50 degrees Centigrade
  6. temperatureAfter heating
  7. stirringstirring
  8. temperatureunder reflux for 5 hours
  9. distillationcontinuing with distillation in vacuo

Sources & evidence

ORD record
ord-0a02e30aa74d42df804b8dd8f5ab522b
Source dataset
uspto-grants-1991_11
Patent number
US05068386

Reaction notes

Loading…