Carbon tetrabromide → HCID 22602342, compound

Temperature

0 °C

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).

1. stirringstirred
2. stirringby stirring the mixture for 15 minutes at 0° C
3. customThe reaction of this mixture
4. customwas terminated by ice-
5. temperaturecooled water (100 ml)
6. stirringafter 20 minutes of stirring
7. customthe organic layer was separated
8. dry with materialThe organic solution was dried (magnesium sulfate)
9. concentrationconcentrated in a vacuum
10. customThe residue was triturated with pentane (1 L), and insoluble Ph3PO
11. customwas removed by filtration
12. concentrationThe filtrate was concentrated in a vacuum
13. washeluted with n-hexane

ORD record

ord-e9e3c05815f4490b8938cec997c791b9

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06835846B2