Реакция #801031

ord-b544cb96e3e54649bdbf8bad2227e0c5

Уравнение реакции

CCCCC/C=C\C/C=C\CCCCCCCCOS(C)(=O)=O
linoleyl methane sulfonate
[Br-].[Li+]
lithium bromide
CCCCC/C=C\C/C=C\CCCCCCCCBr
yellowish oil
Выход 117.2%
CCCCC/C=C\C/C=C\CCCCCCCCBr
Linoleyl Bromide
Выход 117.2%

Реагенты

Нет

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ФильтрацияThe resulting suspension was filtered
  2. 2
    Промывкаthe solid washed with acetone
  3. 3
    ПромывкаThe filtrate and wash
  4. 4
    Другоеsolvent evaporated
  5. 5
    workup.ADDITIONThe resulting residual was treated with water (300 mL)
  6. 6
    ЭкстракцияThe aqueous phase was extracted with ether (3×150 mL)
  7. 7
    ПромывкаThe combined ether phase was washed with water (200 mL), brine (200 mL)
  8. 8
    Сушкаdried over anhydrous Na2SO4
  9. 9
    ДругоеThe solvent was evaporated

Методика

A mixture of linoleyl methane sulfonate (26.6 g, 77.2 mmol) and lithium bromide (30.5 g, 350 mmol) in acetone (350 mL) was stirred under nitrogen for two days. The resulting suspension was filtered and the solid washed with acetone. The filtrate and wash were combined and solvent evaporated. The resulting residual was treated with water (300 mL). The aqueous phase was extracted with ether (3×150 mL). The combined ether phase was washed with water (200 mL), brine (200 mL) and dried over anhydrous Na2SO4. The solvent was evaporated to afford 29.8 g of yellowish oil. The crude product was purified by column chromatography on silica gel (230-400 mesh, 700 mL) eluted with hexanes. This gave 20.8 g (82%) of linoleyl bromide (II).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US09186325B2uspto-grants-2015_11