Pyridine → silane, (4-bromo-1-butynyl)trimethyl-

HRID 1460961Notes

Reaction equation

HRID 1460961 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[C:3]#[C:4][CH2:5][CH2:6]O.N1C=CC=CC=1.P(Br)(Br)[Br:17]>C(OCC)C>[Br:17][CH2:6][CH2:5][C:4]#[C:3][Si:2]([CH3:9])([CH3:8])[CH3:1]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 27608274-Trimethylsilyl-3-butyn-1-ol

Product 1

HCID 642593silane, (4-bromo-1-butynyl)trimethyl-Yield 117%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Trimethylsilyl-3-butyne-1-ol (14.2 g, 0.1 mol) and 0.2 ml of pyridine were dissolved in 50 ml of diethyl ether under a nitrogen atmosphere. Phosphorus tribromide (3.8 ml, 0.04 mol) was slowly added and the mixture was heated under reflux for two hours. Isolation of the product by conventional means yielded 9.6 g of 4-bromo-1-trimethylsilyl-1-butyne as a clear liquid, bp 35°-38° C. at 1 mm Hg.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for two hours

Sources & evidence

ORD record
ord-f26d1150289c42f08114e986d07ac92f
Source dataset
uspto-grants-1991_12
Patent number
US05073561

Reaction notes

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