Bis(2-bromoethyl) ether → HCID 11617610, compound

Participants

Reaction Conditions

Reaction Steps

N-(2-Amino-4-bromo-6-methyl-phenyl)-3,3-dimethyl-butyramide (1v, 1.01 g), N,N-diisopropyl-ethylamine (1.80 mL) and bis(2-bromoethyl)ether (0.50 mL) were dissolved in dry N,N-dimethylformamide (5 mL) and heated to 180° C. for 50 minutes in a sealed microwave process vial. Saturated aqueous sodium bicarbonate (20 mL) was added and the mixture was extracted with ethyl acetate (3×20 mL), the combined organic phases were dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography to furnish 0.740 g (60% yield) of the title compound as a white solid. LC-MS (m/z) 370 (MH+); tR=3.05, (UV, ELSD) 95%, 99%. 1H NMR (500 MHz, DMSO-d6): 1.05 (s, 9H), 2.09 (s, 3H), 2.23 (s, 2H), 2.80 (t, 4H), 3.69 (t, 4H), 7.03 (d, 1H), 7.15 (d, 1H), 8.99 (s, 1H).

Provenance & Evidence