Magnesium Bromide → HCID 90819939, compound

HRID 713859Notes

Reaction equation

HRID 713859 reaction equation
CS([O:5][C:6](=O)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])(=O)=O.[Br-:29].[Mg+2].[Br-]>CCOCC>[C:6]([Br:29])(=[O:5])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 82241Magnesium BromideHCID 87372444HCID 87372444, compound

Product 1

HCID 90819939HCID 90819939, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of docosahexaenoyl methane sulfonate (2.0 g, 5.1 mmol) and magnesium bromide (4.3 g, 23 mmol) in anhydrous ether (100 mL) was stirred under argon overnight. The resulting suspension was filtered and the solid washed with ether (2×30 mL). The filtrate and wash were combined and solvent evaporated. The resulting residual was purified by column chromatography on silica gel (230-400 mesh, 40 mL) eluted with hexanes. This gave 2.2 g of docosahexaenoyl bromide (II) as colourless oil.

Workup

  1. filtrationThe resulting suspension was filtered
  2. washthe solid washed with ether (2×30 mL)
  3. washThe filtrate and wash
  4. customsolvent evaporated
  5. customThe resulting residual was purified by column chromatography on silica gel (230-400 mesh, 40 mL)
  6. washeluted with hexanes

Sources & evidence

ORD record
ord-9939cf78eef94d96ad2a1e109ad8ca10
Source dataset
uspto-grants-2015_11
Patent number
US09186325B2

Reaction notes

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