Bis(2-bromoethyl) ether → HCID 71599638, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-bromo-3-(3-chloro-2-methylbenzyl)-2-methyl-3H-benzo[d]imidazol-5-amine (85 g, 233 mmol), 1-bromo-2-(2-bromoethoxy)ethane (108 g, 466 mmol) and DIPEA (60 g, 466 mmol) in ethylene glycol (1 L) was stirred at 100° C. for 18 h. It was cooled to rt, and diluted with water (1 L) and extracted with DCM (500 mL×4). The combined organic layers were washed with brine, dried over sodium sulphate and evaporated. The residue was purified by column chromatography (eluted with petroleum ether/ethyl acetate=1/1) to give the product (48 g, 47.5%) as a yellow solid; LC/MS: MS (ES+) m/e 434 [M+H]+; 1H NMR (300 MHz, DMSO-d6) δ ppm 2.36 (s, 3H), 2.46 (s, 3H), 3.04-3.07 (m, 4H), 3.68-3.72 (m, 4H), 5.47 (s, 2H), 6.04 (d, J=8.1 Hz, 1H), 6.96 (d, J=2.1 Hz, 1H), 7.06 (t, J=8.1 Hz, 1H), 7.09 (d, J=2.1 Hz, 1H), 7.35 (d, J=8.1 Hz, 1H).

Provenance & Evidence