Bis(2-bromoethyl) ether → HCID 67099953, compound

Participants

Reaction Steps

A mixture of ethyl 2-(3-chloro-2-iodophenyl)acetate (1.3 g, 4.0 mmol) in 6 mL DMF was stirred at room temperature and treated with sodium hydride (0.23 g, 10 mmol). The mixture turned orange, was stirred for 10 minutes, and was treated with 1-bromo-2-(2-bromoethoxy)ethane (1.2 g, 5.2 mmol) in 6 mL DMF dropwise. The mixture was then stirred at room temperature for 2.5 hours. The mixture was carefully quenched with 20 mL H2O and extracted with ether (3×100 mL). The combined organic layers were washed with water (3×50 mL), 20 mL saturated NaCl, dried over anhydrous Na2SO4, and concentrated. The crude product was purified by column eluting with (10-20% EtOAc/hexane) to give the title compound in 0.57 g. MS m/e: (M+H)+ 395.

Provenance & Evidence