Silane, dichloro(3-chloropropyl)phenyl- → 1-Chloro-1-phenylsiletane

HRID 257118Notes

Reaction equation

HRID 257118 reaction equation
[Mg].Cl[CH2:3][CH2:4][CH2:5][Si:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([Cl:8])Cl>C(OCC)C.II>[Cl:8][Si:6]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 76941Silane, dichloro(3-chloropropyl)phenyl-HCID 5462224Magnesium2×

Product 1

HCID 125979911-Chloro-1-phenylsiletaneYield 60.2%

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 3283Diethyl EtherSolvent3×

Procedure

A dry 1 L three neck round bottom flask equipped with a mechanical stirrer, dropping funnel, and condenser with nitrogen inlet system was charged with 18.3 g (0.75 mole) magnesium powder and 250 ml anhydrous diethyl ether. The magnesium was activated by the addition of 200 mg iodine. And then 50.7 g (0.20 mole)(3-chloropropyl)phenyldichlorosilane in 100 ml diethyl ether was added dropwise over 40 mins. at room temperature. The mixture was stirred for an additional 48 h and 200 ml anhydrous diethyl ether was added. The magnesium chloride and excess magnesium was filtered under nitrogen. The solid was washed with three portions of ether. The solvent was removed by the distillation and the product was distilled by reduced pressure. 22 g of 1-chloro-1-phenyl-1-silacyclobutane b.p. 83°-85° C./2 mm Hg was obtained.

Workup

  1. customat room temperature
  2. filtrationThe magnesium chloride and excess magnesium was filtered under nitrogen
  3. washThe solid was washed with three portions of ether
  4. customThe solvent was removed by the distillation
  5. distillationthe product was distilled by reduced pressure

Sources & evidence

ORD record
ord-b15039887b9f42808bf69473c1ffd22a
Source dataset
uspto-grants-1993_11
Patent number
US05260377

Reaction notes

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