Phosphorus tribromide → HCID 13044965, compound

HRID 745684Notes

Reaction equation

HRID 745684 reaction equation
P(Br)(Br)[Br:2].[CH2:5](O)[C:6]#[C:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>CCOCC.N1C=CC=CC=1>[Br:2][CH2:5][C:6]#[C:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 13044963(Z,Z)-5,8-tetradecadien-2-yn-1-ol

Product 1

HCID 13044965HCID 13044965, compoundYield 236.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
23 °C

Procedure

A solution of phosphorous tribromide (0.47 g, 1.73 mmol) in absolute ether (0.5 ml) was added dropwise during five minutes to a mixture of (Z,Z)-5,8-tetradecadien-2-yn-1-ol (1.03 g, 5 mmol), and dry pyridine (14 mg, 0.18 mmol) in 8 ml of absolute ether. The reaction mixture was heated under reflux for 2.5 h, cooled to 23° C., then poured onto ice-water. It was extracted three times with ether. The combined ether extracts were washed with dilute aqueous sodium bicarbonate solution, water, dried over Na2SO4 and concentrated in vacuo. Evaporative distillation of the crude product at 145°-148° C./0.15 mm afforded 1.1 g (80.5%) of (Z,Z)-1-bromo-5,8-tetradecadien-2-yne as a pale yellow oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2.5 h
  3. additionpoured onto ice-water
  4. extractionIt was extracted three times with ether
  5. washThe combined ether extracts were washed with dilute aqueous sodium bicarbonate solution, water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. distillationEvaporative distillation of the crude product at 145°-148° C./0.15 mm

Sources & evidence

ORD record
ord-14a410e1266f4e68b7a037b37326b820
Source dataset
uspto-grants-1986_07
Patent number
US04599443

Reaction notes

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