Bromine → 5-Bromo-3-phenoxypyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

A 3 L flask was charged with 3-phenoxypyridin-2-amine (63.6 g, 342 mmol) and CHCl3 (1500 mL). The reaction was cooled to 0° C. and bromine (21.0 mL, 410 mmol) was added dropwise. The reaction was stirred for 1 hour. Another 1 mL of bromine was added and the reaction was poured into saturated aqueous NaHCO3 (1500 mL) and extracted with CH2Cl2. The organic layer was dried with sodium sulfate and 25 g charcoal. The mixture was filtered through Celite and concentrated in vacuo. The residue was dissolved in CH2Cl2 and passed through a plug of silica (1 L) eluting with 30% EtOAc/Hexanes to afford 5-bromo-3-phenoxypyridin-2-amine (64.02 g, 70.70% yield).

Provenance & Evidence