Allyl bromide → HCID 59588984, compound

Participants

Reaction Steps

A stirred solution of (E)-tert-butyl-N-(3-fluoro-4-bromobut-2-enyl)carbamate (3.48 g, 13 mmol), N-cyclohexyl-4-hydroxybenzamide (3.55 g, 16.2 mmol) and potassium carbonate (2.76 g, 20 mmol) in DMF (10 mL) under nitrogen was heated at 60° C. for 3 hours at which time TLC analysis showed no remaining allyl bromide. The reaction mixture was allowed to cool and then water (50 mL) added, causing a white precipitate to form. Stirred for 30 minutes, then filtered, washing with water to remove any remaining DMF from the filtercake. The precipitate was then taken up into dichloromethane (150 mL), filtered to remove any insolubles and then washed with NaOH solution (2 M; 20 mL) and brine (20 mL). Dried over MgSO4, filtered and the solvent removed under reduced pressure to afford the title compound as a white solid (4.23 g, 80%); 1H-NMR (400 MHz, CDCl3): δppm: 1.21-1.25 (3H, m), 1.40-1.46 (2H, m), 1.44 (9H, s), 1.61-1.69 (1H, m), 1.73-1.77 (2H, m), 2.01-2.05 (2H, m), 3.80 (2H, t, J 6.7 Hz), 3.96 (1H, m), 4.64 (1H, br s), 4.73 (2H, d, J 19.0 Hz), 5.46 (1H, dt J 18.9, 8.1 Hz), 5.81 (1H, br s), 6.96 (2H, d, J 8.3 Hz), 7.73 (2H, d, J 8.3 Hz).

Provenance & Evidence