Sodium Chloride → 3-(Ethylphenyl)-1,1-dichloro-1-silabutane

HRID 259879

Reaction equation

HRID 259879 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:13]([SiH:16]([Cl:18])[Cl:17])[CH:14]=[CH2:15].[Cl-].[Na+]>>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:14]([CH3:15])[CH2:13][SiH:16]([Cl:18])[Cl:17])[CH3:2]

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 7500Ethylbenzene2×HCID 77536Dichloro(prop-2-enyl)silaneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 149720323-(Ethylphenyl)-1,1-dichloro-1-silabutaneYield 77.6%

Conditions

Temperature
50 °C

Procedure

In the same apparatus and procedures as EXAMPLE 1, 27 g (255 mmol) of ethylbenzene and 1.1 g (9.0 mmol) of aluminum chloride were placed. The flask was then immersed in an ice water bath. To the reaction mixture was slowly added dropwise 12.0 g (85 mmol) of allyldichlorosilane and the solution was stirred for an hour. After confirming that no ethylbenzene was left by gas chromatography, 2.4 g, (413 mmol) of sodium chloride was added to reaction mixture, warmed up to 50° C. and stirred for two hours to deactivate the catalyst. Vacuum distillation of the reaction products gave 16.3 g (bp 80°-84° C./0.6 mmHg) of 3-(ethylphenyl)-1,1-dichloro-1-silabutane.

Workup

  1. customThe flask was then immersed in an ice water bath
  2. additionwas added to reaction mixture
  3. stirringstirred for two hours
  4. distillationVacuum distillation of the reaction products

Sources & evidence

ORD record
ord-fc9b1061219c4219a6899b476cae4f23
Source dataset
uspto-grants-1996_06
Patent number
US05523444

Linked notes

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