Triphenylphosphane dibromide → {3-(Triallylsilyl)propyl}(bromo)dimethylsilane

HRID 589226Notes

Reaction equation

HRID 589226 reaction equation
[Br-:1].[Br-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:22]([Si:25]([CH2:37][CH:38]=[CH2:39])([CH2:34][CH:35]=[CH2:36])[CH2:26][CH2:27][CH2:28][Si:29](OC)([CH3:31])[CH3:30])[CH:23]=[CH2:24]>ClCCl>[CH2:22]([Si:25]([CH2:37][CH:38]=[CH2:39])([CH2:34][CH:35]=[CH2:36])[CH2:26][CH2:27][CH2:28][Si:29]([Br:1])([CH3:31])[CH3:30])[CH:23]=[CH2:24]

Participants

4

Reactant 2

HCID 12890784Triphenylphosphane dibromideHCID 86726597{3-(Triallylsilyl)propyl}(methoxy)dimethylsilane

Product 1

HCID 86726598{3-(Triallylsilyl)propyl}(bromo)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To triphenylphosphine dibromide (2.3 g, 5.5 mmol), distilled dichloromethane (15 ml) was added under a nitrogen atmosphere, to dissolve. Then, a solution, in which {3-(triallylsilyl)propyl}(methoxy)dimethylsilane (32) (1.5 g, 5.0 mmol) is dissolved in distilled dichloromethane (5 ml), was added and stirred at room temperature for 5 hours to obtain {3-(triallylsilyl)propyl}(bromo)dimethylsilane (33). After stirring, glass beads which was treated with Piranha solution was added and stirred further at room temperature for 4 hours. Water was added to the reaction mixture to stop the reaction, then 10% hydrochloric acid was added until the salt was dissolved. After that, glass beads were filtered out and washed each three times with toluene, ethanol and diethyl ether, dried, obtaining a functional material (34) represented by the following chemical reaction equation.

Workup

  1. additionwas added under a nitrogen atmosphere
  2. dissolutionto dissolve
  3. additionwas added

Sources & evidence

ORD record
ord-8f1ef9220cc74705839ca9627955ea7b
Source dataset
uspto-grants-2016_01
Patent number
US09228107B2

Reaction notes

Loading…