1-Ethenyl-4-methylbenzene → 1-Methyl-4-[2-(trichlorosilyl)ethyl]benzene

HRID 1099000Notes

Reaction equation

HRID 1099000 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.[Cl:10][SiH:11]([Cl:13])[Cl:12]>C1C2NC3C(=CC=CC=3)SC=2C=CC=1>[C:2]1([CH3:1])[CH:9]=[CH:8][C:5]([CH2:6][CH2:7][Si:11]([Cl:13])([Cl:12])[Cl:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 121611-Ethenyl-4-methylbenzeneHCID 24811Trichlorosilane

Product 1

HCID 121594721-Methyl-4-[2-(trichlorosilyl)ethyl]benzeneYield 98%

Reagents, catalysts & solvents 1

HCID 7108PhenothiazineCatalyst

Conditions

Temperature
70 °C

Procedure

Into a 3 liter round-bottom flask fitted with a reflux condenser, addition funnel and magnetic stir bar, was charged 4-methylstyrene (904.4 g, 7.65 mols), VCAT (2.25 g, 50 ppm) and phenothiazine (1.94 g, 1000 ppm). The reaction mixture was heated to 70° C. and then trichlorosilane (1036.6 g, 7.65 mols) was added dropwise to the reaction mixture. During the addition, the reaction mixture was maintained between 80 to 100° C. After the addition was finished, the reaction mixture was kept at 70° C. for additional two hours. After distillation, >98% pure (2-p-tolyl-ethyl)trichlorosilane (1565 g, 6.19 mols) was obtained (collected at 75° C./1 mmHg). The product structure was characterized by GC-MS.

Workup

  1. customInto a 3 liter round-bottom flask fitted with a reflux condenser, addition funnel and magnetic stir bar
  2. additionDuring the addition
  3. temperaturethe reaction mixture was maintained between 80 to 100° C
  4. additionAfter the addition
  5. distillationAfter distillation

Sources & evidence

ORD record
ord-2ec0be95778d488ea8a957fdc208569d
Source dataset
uspto-grants-2012_03
Patent number
US08143336B2

Reaction notes

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