Vinyltrichlorosilane → Pentakis(trichlorosilylethyl)-n-butylbenzene

HRID 1834

Reaction equation

HRID 1834 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1.[CH:11]([Si:13]([Cl:16])([Cl:15])[Cl:14])=[CH2:12]>[Cl-].[Al+3].[Cl-].[Cl-]>[Cl:14][Si:13]([CH2:11][CH2:12][C:10]1[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])=[C:6]([CH2:12][CH2:11][Si:13]([Cl:16])([Cl:15])[Cl:14])[C:7]([CH2:12][CH2:11][Si:13]([Cl:16])([Cl:15])[Cl:14])=[C:8]([CH2:12][CH2:11][Si:13]([Cl:16])([Cl:15])[Cl:14])[C:9]=1[CH2:12][CH2:11][Si:13]([Cl:16])([Cl:15])[Cl:14])([Cl:16])[Cl:15]

Participants

4

Reactant 2

HCID 6413VinyltrichlorosilaneHCID 7705Butylbenzene

Product 1

HCID 53921007Pentakis(trichlorosilylethyl)-n-butylbenzeneYield 102.2%

Reagents, catalysts & solvents 1

HCID 6451240Aluminum(III) ChlorideCatalyst

Procedure

In the same apparatus and by the same procedure described in EXAMPLE 1, n-butylbenzene 0.86 g (6.40 mmol), vinyltrichlorosilane 5.17 g (32.00 mmol) and aluminum chloride 0.047 g (0.35 mmol) were reacted at 80° C. for 6 hours under a dry nitrogen atmosphere. Recrystallization of solid product from THF gave 6.16 g (yield: 2.68%, mp: 228°-35° C.) of pentakis(trichlorosilylethyl)-n-butylbenzene. Distillation of the filtrate gave 2.20 g (yield: 36.59%, bp: 192°-8° C./0.6 mm), 1.81 g (yield: 30.0%, bp: 220°-5° C./0-6 mm), 0.63 g (yield: 10.15%), 0.12 g (yield: 2.05%) and 0.22 g (yield: 3.59%) of tris-, tetrakis(trichlorosilylethyl)-n-butylbenzenes, tetrakis(trichlorosilylethyl)dibutylbenzene, mono- and bis(trichlorosilylethyl)benzenes, respectively. isomeric mixtures were also obtained. NMR data of the polyalkylated products prepared as above are listed in Table 13.

Workup

  1. customwere reacted at 80° C. for 6 hours under a dry nitrogen atmosphere
  2. customRecrystallization of solid product from THF

Sources & evidence

ORD record
ord-614e99a357bf4013896cb29a932850fc
Source dataset
uspto-grants-1998_03
Patent number
US05726336

Linked notes

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