1-Ethenyl-4-methylbenzene → HCID 22373345, compound

HRID 1098999Notes

Reaction equation

HRID 1098999 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]>C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:2]1([CH3:1])[CH:9]=[CH:8][C:5]([CH:6]([Si:11]([Cl:13])([Cl:12])[Cl:10])[CH3:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 121611-Ethenyl-4-methylbenzeneHCID 24811Trichlorosilane

Product 1

HCID 22373345HCID 22373345, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 178419050HCID 178419050, compoundCatalyst

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 (900 g, 7.6 mols) and Bis(triphenylphosphine)palladium (II) dichloride (1.8 g, 0.2% wt). The reaction mixture was heated to 70° C. and then trichlorosilane (1031 g, 7.6 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, pure (1-p-tolyl-ethyl)trichlorosilane (1400 g, 5.53 mols) was obtained (collected at 75° C./1 mmHg). The product structure was characterized by GC-MS and 13C NMR (δ˜14 ppm, CDCl3, Cl3Si—CH (CH3)-Ph; δ˜35 ppm, CDCl3, Cl3Si—CH(CH3)-Ph).

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-8f4c7fd74c3c40e295f9dbe389c9c33a
Source dataset
uspto-grants-2012_03
Patent number
US08143336B2

Reaction notes

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