Triphenylphosphine → HCID 11010750, compound

Temperature

0 °C

An acetonitrile solution (100 ml) of triphenylphosphine (18.6 g, 70.9 mmols) was stirred at 0° C. Bromine (11.4 g, 3.7 ml, 71.3 mmols) was slowly blended into the solution. To the mixture, an acetonitrile (30 ml) solution of (E)-3-methyl-2-dodecen-1-ol (3′) was added dropwise, followed by stirring for 2 hours at 0° C. The solvent was removed under vacuum, and the residue was dissolved in dichloromethane. The solution was washed with saturated sodium bicarbonate and a saturated aqueous solution of sodium chloride, then dried over sodium sulfate, and concentrated. Pentane was added to the residue, and a solid formed was removed by filtration. The filtrate was concentrated in a vacuum to obtain 17.9 g (97%) of (E)-1-bromo-3-methyl-2-dodecene (4′).

1. customThe solvent was removed under vacuum
2. dissolutionthe residue was dissolved in dichloromethane
3. washThe solution was washed with saturated sodium bicarbonate
4. dry with materiala saturated aqueous solution of sodium chloride, then dried over sodium sulfate
5. concentrationconcentrated
6. additionPentane was added to the residue
7. customa solid formed
8. customwas removed by filtration
9. concentrationThe filtrate was concentrated in a vacuum

ORD record

ord-88b57f4d56a8492a8bb56e926e21c6c8

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06835846B2