Hydrochloric Acid → HCID 67856162, compound

Participants

Reaction Steps

Sodium hydride (0.21 g, 7.02 mmol, 80% dispersion in mineral oil) was added to a stirred, room temperature solution of (VII) (1.40 g, 5.85 mmol) and dry ethanol (0.38 mL), 6.44 mmol) in DMF (8 mL). An exotherm resulted and after 10 min, 4-bromo-2-fluorobenzyl bromide (1.72 g, 6.44 mmol) was added. After 2 h, the reaction mixture was added to an aqueous solution consisting of 10% aq. HCl (25 mL) and water (125 mL). This was extracted with ether (150 mL) and the ether extract was washed with brine (150 mL) and silica gel (25 mL) was added to it. The ether was removed and the silica adsorbate was flash chromatographed (7:3 petroleum ether: ethyl acetate) to provide the title compound as an oil (1.89 g, 68%): NMR (CDCl3, 300 MHz): d 7.89 (m, 1H, ArH), 7.70 (m, 2H, ArH), 7.55 (m, 2H, ArH), 7.26 (m, 2H, ArH), 4.60 (d, 1H, J=16.7 Hz, NCH2), 4.50 (d, 1H, J=16.7 Hz, NCH2), 4.05 (m, 2H, CO2CH2), 3.22 (m, 1H, OCH2), 2.94 (m, 1H, OCH2), 1.11 (t, 3H, CH3), 1.05 (t, 3H, CH3); IR (neat, cm-1): 1750: MS (+FAB): 472, 474 (MH+, 5%), 426, 428 (35%), 398, 400 (20%), 187, 189 (100%).

Provenance & Evidence