Carbon tetrabromide → HCID 22602342, compound

Participants

Reaction Conditions

Reaction Steps

A dichloromethane solution (100 ml) of CBr4 (85 g, 256 mmols) was added dropwise to a stirred and ice-cooled dichloromethane solution (300 ml) of Ph3P (138 g, 526 mmols). To the mixture, a dichloromethane solution (100 ml) of the (E)-5-methyl-4-tetradecenal (5) (29.0 g, 129 mmols) was added while being cooled at 0° C. and stirred, followed by stirring the mixture for 15 minutes at 0° C. The reaction of this mixture was terminated by ice-cooled water (100 ml), and after 20 minutes of stirring, the organic layer was separated. The organic solution was dried (magnesium sulfate), and then concentrated in a vacuum. The residue was triturated with pentane (1 L), and insoluble Ph3PO was removed by filtration. The filtrate was concentrated in a vacuum, and then the oily residue was subjected to silica gel column chromatography, and eluted with n-hexane to obtain 38.1 g (77.6%) of oily (E)-1,1-dibromo-6-methyl-1,5-pentadecadiene (6).

Provenance & Evidence