2-Norbornene → HCID 17865598, compound

HRID 1816078Notes

Reaction equation

HRID 1816078 reaction equation
[Cl:1][SiH2:2][Cl:3].[CH:4]12[CH2:10][CH:7]([CH2:8][CH2:9]1)[CH:6]=[CH:5]2>C1(C)C(C)=CC=CC=1.[Pt]>[CH:4]12[CH2:10][CH:7]([CH2:8][CH2:9]1)[CH2:6][CH:5]2[Si:2]([CH:5]1[CH2:6][CH:7]2[CH2:10][CH:4]1[CH2:9][CH2:8]2)([Cl:3])[Cl:1]

Participants

5

Reactant 2

HCID 103522-Norbornene2×HCID 61330Dichlorosilane

Product 1

HCID 17865598HCID 17865598, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
80 °C

Procedure

Dichlorosilane (18.5 g, 0.18 mol) is condensed into a cold trap at −78° C. and dissolved in precooled xylene (200 ml). The temperature is −10° C. after the addition. First norbornene (34.5 g, 0.37 mol) and then the catalyst [COD]PtCl2 (1% solution in in CH2Cl2, 2.50 ml) are added, whereupon an exothermic reaction starts spontaneously. The temperature rises to 46° C. and an ice bath is used to reduce the temperature to 40° C. After 15 min, the temperature begins to fall again. According to GC (gas chromatography), about 50% of the norbornene is consumed. The reaction mixture is heated to 80° C. for 15 min, then held at 40° C. for a further 1.5 h. The conversion of the norbornene according to GC is >90%. The reaction mixture is fractionally distilled. The main fraction at b.p. 118° C./1 mbar consists of 49.8 g of dichlorodinorbornylsilane. Yield 94%. Purity 95.7% (GC).

Workup

  1. customcondensed into a cold trap at −78° C.
  2. customis −10° C.
  3. additionafter the addition
  4. customrises to 46° C.
  5. customan ice bath is used
  6. customto 40° C
  7. customis consumed
  8. waitheld at 40° C. for a further 1.5 h
  9. distillationThe reaction mixture is fractionally distilled

Sources & evidence

ORD record
ord-ffe04dd1eb2d48248149be5152489549
Source dataset
uspto-grants-2005_04
Patent number
US06881855B2

Reaction notes

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