Phosphorus tribromide → HCID 86747279, compound

HRID 1735174Notes

Reaction equation

HRID 1735174 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[CH2:3][C:4]#[C:5][CH2:6]O.P(Br)(Br)[Br:11]>C(OCC)C>[Br:11][CH2:6][C:5]#[C:4][CH2:3][Si:2]([CH3:9])([CH3:8])[CH3:1].[Br-:11]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 13214509HCID 13214509, compound

Product 1

HCID 86747279HCID 86747279, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-(trimethylsilyl)-2-butynol [J. Pernet, B. Randrianoelina, and L. Miginiac, Tetrahedron Letters, 25, 651, (1984)] (10 g, 70 mmol) is dissolved in dry diethyl ether (150 ml) and phosphorous tribromide (2.2 ml, 23.3 mmol) is added dropwise. Then the mixture is refluxed, protected from the light during 2.5 hours. The reaction is washed twice with water, once with aqueous sodium bicarbonate and then once with water. The organic layer is dried over sodium sulfate. The solvent is evaporated under reduced pressure to afford the expected bromide (4-bromo-2-butynyl)trimethylsilane (1.4 g, 97%) which is used without purification.

Workup

  1. temperatureThen the mixture is refluxed
  2. washThe reaction is washed twice with water, once with aqueous sodium bicarbonate
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. customThe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-15c806ebab184aa0b0999e419e9e75c5
Source dataset
uspto-grants-1996_07
Patent number
US05536732

Reaction notes

Loading…