Phosphorus tribromide → 3-(Bromomethyl)-2-chloropyridine

Participants

Reaction Conditions

Reaction Steps

In a 250 mL round bottom flask was dissolved (2-chloropyridin-3-yl)methanol (6.7 g, 47 mmol) in CH2Cl2 (100 mL). The reaction was cooled to 0° C., to which was slowly added tribromophosphine (4.8 mL, 51 mmol), and allowed to warm to RT overnight. The reaction was quenched by addition of ice, extracted into CH2Cl2, washed 1×NaHCO3, 2×H2O, dried with Mg2SO4, filtered through fritted funnel and filtrate was concentrated. The crude was purified by silica gel chromatography eluting with 15-45% EtOAc/Hex. The product fraction were concentrated down to yield 3-(bromomethyl)-2-chloropyridine as off-white solid. MS m/z=206, 208 [M+1]+. Calc'd for C6H5BrClN: 206.47.

Provenance & Evidence