Magnesium Bromide → (5Z,8Z,11Z,14Z)-1-bromoicosa-5,8,11,14-tetraene

HRID 713841Notes

Reaction equation

HRID 713841 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])(=O)=O.[Br-:26].[Mg+2].[Br-]>CCOCC>[CH2:6]([Br:26])[CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 82241Magnesium BromideHCID 11122179Arachidonyl methane sulfonate

Product 1

HCID 58559546(5Z,8Z,11Z,14Z)-1-bromoicosa-5,8,11,14-tetraene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of arachidonyl methane sulfonate (1.0 g, 2.7 mmol) and magnesium bromide (2.2 g, 12 mmol) in anhydrous ether (40 mL) was stirred under argon for two days. The resulting suspension was filtered and the solid washed with ether (2×10 mL). The filtrate and wash were combined and solvent evaporated. The resulting residual was treated with hexanes (50 mL). The solid was filtered and solvent evaporated resulting in an oily residual. The crude product was purified by column chromatography on silica gel (230-400 mesh, 30 mL) eluted with hexanes. This gave 1 g of arachidonyl bromide (II) as colourless oil.

Workup

  1. filtrationThe resulting suspension was filtered
  2. washthe solid washed with ether (2×10 mL)
  3. washThe filtrate and wash
  4. customsolvent evaporated
  5. additionThe resulting residual was treated with hexanes (50 mL)
  6. filtrationThe solid was filtered
  7. customsolvent evaporated
  8. customresulting in an oily residual
  9. customThe crude product was purified by column chromatography on silica gel (230-400 mesh, 30 mL)
  10. washeluted with hexanes

Sources & evidence

ORD record
ord-4a194668fe784e529367e0d02625ab9a
Source dataset
uspto-grants-2015_11
Patent number
US09186325B2

Reaction notes

Loading…