Phosphorus tribromide → 6-(Bromomethyl)-2-(2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine

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Reaction Steps

To a solution of (2-(2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl)methanol (148 g, 0.584 mol) in DCM (2.96 L) is added PBr3 (237.3 g, 0.877 mol) at −40° C. The reaction mixture is allowed to warm to temperature and then stirred for a further for 2 hours at room temperature. The reaction is cooled to 0° C., quenched with ice cold water (1.5 L) and saturated sodium bicarbonate solution is added to adjust the pH ˜7.5 to 8. The mixture is diluted with DCM (2 L), the aqueous layer is separated and extracted with DCM (3 L). The organic extracts are combined, washed with water (2×3 L) and brine solution (3 L), dried the organic extracts over sodium sulphate, filtered and evaporated to dryness to give the title compound (140 g, 76%). LCMS m/z 316/318 79Br/81Br (M+H)+.

Provenance & Evidence