Diethyl Ether → 4-Decyne, 1-bromo-

HRID 840063Notes

Reaction equation

HRID 840063 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[Br-:12].[Li+].CCOCC>C1COCC1>[Br:12][CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 82050Lithium BromideHCID 1413221-Chloro-4-decyne2×

Product 1

HCID 226216834-Decyne, 1-bromo-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Bromodec-4-yne was prepared from 1-chlorodec-4-yne. The 1-chlorodec-4-yne (10.6 g, 61 mmol) and 25 g of lithium bromide were refluxed in 80 ml of THF for 21 hours. The conversion was 74%. Ether was added, the reaction mixture was washed with water (2×) and brine, dried over magnesium sulfate and stripped. The product was dissolved in 70 ml of THF and refluxed for 8 hours with an additional 25 g of lithium bromide. This gave 95% conversion of the chloride to the bromide. The same workup provided 11.36 g of 1-bromodec-4-yne.

Workup

  1. washthe reaction mixture was washed with water (2×) and brine
  2. dry with materialdried over magnesium sulfate
  3. dissolutionThe product was dissolved in 70 ml of THF
  4. temperaturerefluxed for 8 hours with an additional 25 g of lithium bromide

Sources & evidence

ORD record
ord-f6c0f997f4574b7d99e3a5984f3dc778
Source dataset
uspto-grants-2002_04
Patent number
US06365549B2

Reaction notes

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