Phosphorus tribromide → HCID 86747279, compound

HRID 1655993Notes

Reaction equation

HRID 1655993 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-e7865a433bc14e3e80954a29f3414d6f
Source dataset
uspto-grants-1993_10
Patent number
US05252587

Reaction notes

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