Lithium Bromide → (6Z,9Z)-18-bromooctadeca-6,9-diene

HRID 713849Notes

Reaction equation

HRID 713849 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(=O)=O.[Br-:24].[Li+]>CC(C)=O>[CH2:6]([Br:24])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 59753235Linoleyl methanesulfonate

Product 1

HCID 10065142(6Z,9Z)-18-bromooctadeca-6,9-dieneYield 117.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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).

Workup

  1. filtrationThe resulting suspension was filtered
  2. washthe solid washed with acetone
  3. washThe filtrate and wash
  4. customsolvent evaporated
  5. additionThe resulting residual was treated with water (300 mL)
  6. extractionThe aqueous phase was extracted with ether (3×150 mL)
  7. washThe combined ether phase was washed with water (200 mL), brine (200 mL)
  8. dry with materialdried over anhydrous Na2SO4
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b544cb96e3e54649bdbf8bad2227e0c5
Source dataset
uspto-grants-2015_11
Patent number
US09186325B2

Reaction notes

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