Toluene → 3-(Methylphenyl)-1,1,1-trichloro-1-silabutane

HRID 259883Notes

Reaction equation

HRID 259883 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-:8].[Al+3].[Cl-].[Cl-].[CH2:12]([SiH:15]([Cl:17])[Cl:16])[CH:13]=[CH2:14].[Cl-].[Na+]>>[CH3:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:13]([CH3:14])[CH2:12][Si:15]([Cl:8])([Cl:17])[Cl:16]

Participants

5

Reactant 4

HCID 1140TolueneHCID 5234Sodium ChlorideHCID 77536Dichloro(prop-2-enyl)silaneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 224018363-(Methylphenyl)-1,1,1-trichloro-1-silabutaneYield 73%

Conditions

Temperature
50 °C

Procedure

In the same apparatus and procedures as EXAMPLE 1, 14.6 g (159 mmol) of toluene and 0.18 g (1.6 mmol) of aluminum chloride were placed and reacted with 5.0 g (32 mmol) of allyldichlorosilane under the dry nitrogen atmosphere for 20 min. After stirring the solution for another an hour, 2.0 g (30 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 6.3 g (bp 73°-76° C./0.5 mmHg) of of 3-(methylphenyl)-1,1,1-trichloro-1-silabutane in 73% yield.

Workup

  1. stirringstirred for two hours
  2. distillationVacuum distillation of the reaction products

Sources & evidence

ORD record
ord-17b603a27a0142f793283a973308d495
Source dataset
uspto-grants-1996_06
Patent number
US05523444

Reaction notes

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