Phosphorus tribromide → (3-Bromoprop-1-yn-1-yl)benzene

Temperature

40 °C

Phosphorous tribromide (2.62 mL, 27.6 mmol) was added to a solution of 3-phenyl-2-propyn-1-ol (10.0 g, 76 mmol) and pyridine (0.14 mL, 1.77 mmol) in diethyl ether (22 mL) at a rate to maintain reflux. After addition, the mixture was heated at 40° C. for 2 h. The mixture was cooled and poured onto ice. The organic layer was separated and diluted with diethyl ether (100 mL), washed with saturated sodium bicarbonate (2×50 mL) and saturated sodium chloride (50 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to afford 1-phenyl-3-bromo-1-propyn (13.4 g, 90%).

1. temperatureto maintain
2. temperaturereflux
3. additionAfter addition
4. temperatureThe mixture was cooled
5. additionpoured onto ice
6. customThe organic layer was separated
7. additiondiluted with diethyl ether (100 mL)
8. washwashed with saturated sodium bicarbonate (2×50 mL) and saturated sodium chloride (50 mL)
9. dry with materialThe organic layer was dried (MgSO4)
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-b64c5801050c4f40b407dc58730dc66f

Source dataset

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05861427