Iodine → N-(1-(4-chlorophenyl)-3-pent-4-enoylcyclobutyl)benzamide

Participants

Reaction Steps

Magnesium powder (1.05 g, 42.0 mmol) was placed into a round-bottomed flask with a small piece of iodine. Dry THF was added to cover the magnesium and the solution was heated to a gentle reflux for 30 minutes. While refluxing, a second solution of 4-bromo-1-buten (4.72 mL, 42.0 mmol) in dry THF (5 mL) was added. After 12 min, the mixture was cooled to room temperature and added to a solution of N-(1-(4-chlorophenyl)-3-(methoxy(methyl)carbamoyl)cyclobutyl)benzamide (1.12 g, 3.0 mmol) in dry THF (30 mL). After 2 h, the reaction was quenched with saturated aqueous NH4Cl. 1M HCl was added to pH-3 and the solution was extracted with diethyl ether (×2). The combined organic layers were washed successively with 1M HCl, water and saturated aqueous sodium chloride, dried over MgSO4, filtered and concentrated to give the crude product that was used to the next step without further purification. 1H NMR (CDCl3, 600 MHz) δ 7.76 (d, J=7.2 Hz, 2H), 7.47-7.50 (m, 1H), 7.46 (d, J=8.7 Hz, 2H), 7.40-7.43 (m, 2H), 7.33 (d, J=8.7 Hz, 2H), 6.77 (s, 1H), 5.72-5.80 (m, 1H), 4.92-5.01 (m, 2H), 3.16-3.22 (m, 1H), 2.90-2.94 (m, 2H), 2.82-2.86 (m, 2H), 2.54 (t, J=7.3 Hz, 2H), 2.30-2.35 (m, 2H). ESI MS found for C22H22ClNO2 m/z [368.4/370.4 (M+1)].

Provenance & Evidence