2-Methoxyethanol → HCID 59352795, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-methoxyethanol (8.81 g, 9.13 ml, 116 mmol) in anhydrous THF (150ml) was added sodium hydride (4.63 g, 116 mmol) under nitrogen at 5° C. or below and the reaction mixture was stirred at 25° C. for 1 h. Then 3-bromo-2-chloro-5-nitropyridine (CAN 5470-17-7) (25 g, 105 mmol) was added drop wise at 25° C. and stirred at 25° C. for 1 h. Ice-water (150 ml) was added to the reaction mixture and extracted with ethyl acetate (500 mL). The combined organic layers was washed with water and brine, dried over Na2SO4 and evaporated under reduced pressure to get the crude residue (25.7 g). The crude was purified by column chromatography (15% ethyl acetate/hexane) to get the desired product (21.6 g, 74%) as light yellow solid; GC/MS (FID/EI): 100%, 276.0 (M)+.

Provenance & Evidence