Triphenylphosphine → 2-(5-Bromopent-1-ynyl)pyridine

Temperatur

5 °C

Br2 (1.11 mL, 21.4 mmol) was added to a solution of triphenylphosphine (8.30 g, 30.7 mmol) in DCM (40 mL) at −5° C. A solution of 5-pyridin-2-yl-pent-4-yn-1-ol (3.00-18.6 mmol) in DCM (10 mL) was added dropwise to the reaction mixture in order to maintain a temperature lower than 5° C. The reaction mixture was stirred for 5 hours at −10° C. and was quenched with a saturated solution of NaHCO3. The aqueous phase was extracted with DCM. The resulting organic phase was washed with brine dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (DCM/MeOH 99.5:0.5) to yield 2-(5-bromo-pent-1-ynyl)-pyridine (1.20 g, 5.35 mmol, 29%) with a purity of 50%.

1. customwas quenched with a saturated solution of NaHCO3
2. extractionThe aqueous phase was extracted with DCM
3. washThe resulting organic phase was washed with brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customevaporated
7. customThe crude residue was purified by flash chromatography (DCM/MeOH 99.5:0.5)

ORD-Eintrag

ord-e81b3580bbb3400388199bf16f58be3c

Quelldatensatz

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08101637B2