Ammonium Chloride → 2-(Benzyloxy)-1-(6-bromo-2-chloropyridin-3-yl)ethanol

Participants

Reaction Conditions

Reaction Steps

6-Bromo-2-chloro-3-iodopyridine (1.50 g, 4.71 mmol) was dissolved in THF (15 mL) and cooled to −78° C., followed by addition of isopropylmagnesium chloride-lithium chloride complex (3.99 mL, 5.18 mmol). The mixture was stirred at −78° C. for 1 h. 2-(benzyloxy)acetaldehyde (0.849 g, 5.65 mmol) was added and the resulting mixture warmed to 0° C. and stirred for 2 h. The mixture was treated with saturated NH4Cl and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to gave 2-(benzyloxy)-1-(6-bromo-2-chloropyridin-3-yl)ethanol (1.54 g, yield: 95%). MS (M+H)+: 344.

Provenance & Evidence