5-Bromo-2-ethoxypyridine

Chemical Properties

Uses

Synthesis

624-28-2

64-17-5

55849-30-4

The general procedure for the synthesis of 5-bromo-2-ethoxypyridine from 2,5-dibromopyridine and ethanol was as follows: freshly cut sodium metal (74 mg, 3.2 mmol) was dissolved in anhydrous ethanol (1.2 mL), followed by the addition of a solution of 2,5-dibromopyridine (236 mg, 1 mmol) in dimethylformamide (DMF, 3 mL). The reaction mixture was stirred at 80 °C for 1 h and subsequently cooled to room temperature. Upon completion of the reaction, the reaction was quenched with deionized water (4 mL) and extracted three times with ether. The organic phases were combined, washed with saturated saline, dried over anhydrous sodium sulfate and subsequently concentrated under reduced pressure. Purification of the residue by fast column chromatography afforded the target product 5-bromo-2-ethoxypyridine as a white solid (192 mg, 95% yield). Mass spectrometry (MS) analysis showed (M+H)+ peaks at m/z 202 and 204.

References