Allyl bromide → HCID 11321547, compound

Participants

Reaction Conditions

Reaction Steps

A dry and argon flushed 10 mL flask, equipped with a magnetic stirrer and a septum, was charged with i-PrMgCl.LiCl (1 mL, 1.05 M in THF, 1.05 mmole), the reaction mixture was cooled to −15° C. and 3,5-dibromopyridine (236.9 mg, 1 mmole) was then added at one portion. The temperature than increased till −10° C. and the Br/Mg-exchange was complete after 15 min (checked by GC analysis of reaction aliquots, conversion more than 98%), allyl bromide (140.6 mg, 1 mmole) was added. The reaction mixture was stirred for 1 h at −10° C. and was then quenched with sat. NH4Cl solution (2 mL). The aqueous phase was extracted with ether (3×4 mL), dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by flash chromatography (dichloromethane) yielding the 3-allyl-5-bromopyridine (2ca) as a colourless oil (184.2 mg, 93%). 1H-NMR (CDCl3, 200 MHz): δ=8.48 (d, J=2.2 Hz, 1H); 8.32 (d, J=1.6 Hz, 1H); 7.61 (dd, J=2.2 Hz, J=1.6 Hz, 1H); 5.89-5.68 (m, 1H); 5.08-5.01 (m, 1H); 3.32 (brd, J=6.8 Hz, 1H).

Provenance & Evidence