4-Bromobenzyl bromide → 1-(4-Bromo-benzyl)-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine (0.40 g, 1.40 mmol) in 2-butanone (30 ml) was added 4-bromobenzyl bromide (0.52 g, 2.1 mmol). The reaction was heated to 90° C. for 16 h. After this time, the resulting suspension was cooled to rt and filtered. The collected solid was washed with additional 2-butanone and then the solid was partitioned between dichloromethane and a saturated solution of NaHCO3. The biphasic mixture was stirred at rt for 10 min and then the organic layer was separated. The aqueous phase was extracted with additional dichloromethane and the combined organic fractions were washed with H2O, dried (Na2SO4), filtered and concentrated under reduced pressure to provide 1-(4-bromo-benzyl)-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine as a white solid (0.532 g, 83%). HPLC-MS 454, 456 [M+1]+.

Provenance & Evidence