Ethyl bromoacetate → HCID 14856507, compound

Participants

Reaction Steps

Under nitrogen, (26) (2.4 g, 8.5 mmoL) was added portionwise to a stirred suspension of sodium hydride (427 mg of a 60% dispersion in mineral oil, 1.25 eq) in dry dimethylformamide (60 mL , from CaH2). After 15 min, ethyl bromoacetate (1.8 g, 10.0 mmoL, 1.25 eq) was added and the mixture was stirred for an additional hour before it was diluted with water (200 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine (3×200 mL), dried (MgSO4), and concentrated. The residue was recrystallized from ethyl acetate/hexane to provide 1.5 g. A sample recrystallized a second time from ethyl acetate/hexane provided the following data: mp 215°-217° C.; IR (KBr) 3357, 3250, 1710, 1160, 828 cm-1 ; 1H NMR (CDCl3, 200 MHz) 7.65 (dd, 2H, J=4.8, 8.6Hz), 7.52 (ddd, 2 H, J= 2.5, 9.3Hz), 7.20 (ddd, 2H, J=2.3, 8.6, 8.6Hz), 3.97 (bs, 2H, exchangeable), 3.75 (q, 2H, J=7.1H), 0.85 (t, 3H, J=7.1Hz); MS m/z 367 (M+), 215 (base peak).

Provenance & Evidence