Реакция #95467

Уравнение реакции

phosphorous tribromide

(Z,Z)-5,8-tetradecadien-2-yn-1-ol

→

(Z,Z)-1-bromo-5,8-tetradecadien-2-yne

Растворители

ether

ether

Условия реакции

Обработка

1. 1
   ТемператураThe reaction mixture was heated
2. 2
   Температураunder reflux for 2.5 h
3. 3
   workup.ADDITIONpoured onto ice-water
4. 4
   ЭкстракцияIt was extracted three times with ether
5. 5
   ПромывкаThe combined ether extracts were washed with dilute aqueous sodium bicarbonate solution, water
6. 6
   Сушкаdried over Na2SO4
7. 7
   Концентрированиеconcentrated in vacuo
8. 8
   workup.DISTILLATIONEvaporative distillation of the crude product at 145°-148° C./0.15 mm

Методика

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.

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