Phosphorus tribromide → (E,E)-1-bromo-2,4-pentadecadien-6,9-diyne

HRID 1106010Notes

Reaction equation

HRID 1106010 reaction equation
[CH2:1]=[CH:2][CH:3](O)/[CH:4]=[CH:5]/[C:6]#[C:7][CH2:8][C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].P(Br)(Br)[Br:18]>CCOCC>[Br:18][CH2:1]/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[C:6]#[C:7][CH2:8][C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 12821660(E)-1,4-pentadecadien-6,9-diyn-3-ol

Product 1

HCID 12821661(E,E)-1-bromo-2,4-pentadecadien-6,9-diyne

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of (E)-1,4-pentadecadien-6,9-diyn-3-ol (8.5 g) in ether (200 mL) was cooled to -40° and treated over 5 min with phosphorous tribromide (3.7 mL) dissolved in ether (70 mL). The cooling bath was removed and the reaction mixture was warmed to 0° over 1 hour and then poured onto ice. The ether extract was then washed with water, sodium carbonate solution (10 mL) and dried (MgSO4). Removal of the solvents and purification of the residue by liquid chromatography (two columns, hexane) gave (E,E)-1-bromo-2,4-pentadecadien-6,9-diyne as pure material (7.8 g).

Workup

  1. customThe cooling bath was removed
  2. temperaturethe reaction mixture was warmed to 0° over 1 hour
  3. additionpoured onto ice
  4. extractionThe ether extract
  5. washwas then washed with water, sodium carbonate solution (10 mL)
  6. dry with materialdried (MgSO4)
  7. customRemoval of the solvents and purification of the residue by liquid chromatography (two columns, hexane)

Sources & evidence

ORD record
ord-cc6f1a6e08864c8aa7a14601caca0de3
Source dataset
uspto-grants-1982_01
Patent number
US04311645

Reaction notes

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