Carbon tetrabromide → 8-bromo-1-octyne

Temperature

0 °C

Dehydrated dichloromethane (20 mL) and triphenylphosphine (5.91 g, 22.5 mmol) were added to 8-hydroxy-1-octyne (1.95 g, 15 mmol). The mixture was cooled to 0° C. and was then dropwise added to dehydrated dichloromethane (10 mL) containing carbon tetrabromide (7.46 g, 22.5 mmol), followed by stirring at room temperature for 2 hours. After separation between dichloromethane (100 mL) and 5% sodium bicarbonate (150 mL), the organic layer was washed with saturated brine (150 mL). The organic layer was dried over sodium sulfate and then concentrated. The concentrated product was purified by silica gel column chromatography (dichloromethane:methanol=from 100:0 to 99:1) to yield 8-bromo-1-octyne (crude).

1. customAfter separation between dichloromethane (100 mL) and 5% sodium bicarbonate (150 mL)
2. washthe organic layer was washed with saturated brine (150 mL)
3. dry with materialThe organic layer was dried over sodium sulfate
4. concentrationconcentrated
5. customThe concentrated product was purified by silica gel column chromatography (dichloromethane:methanol=from 100:0 to 99:1)

ORD record

ord-8a9170777c2941e5a40482710d0bd2a1

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09285319B2