1-Bromo-3-chloropropane → HCID 57517460, compound

Participants

Reaction Steps

To a mixture of 2-nitro-N-(prop-2-yn-1-yl)benzenesulfonamide (1.08 g, 4.48 mmol) and cesium carbonate (7.30 g, 22.42 mmol) in acetone (40 mL) was added neat 1-bromo-3-chloropropane (6.5 mL, 66 mmol) dropwise. Upon complete addition, the reaction mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated and the residue partitioned between EtOAc (25 mL) and water (15 mL). The aqueous layer was extracted with additional EtOAc (20 mL), the combined organic layers dried over anhydrous MgSO4 and concentrated. Purification via silica chromatography (25-40% EtOAc/hexane) afforded Intermediate 18 as an oil (0.9764 g, 69%). 1H NMR (400 MHz, CDCl3) δ 8.10-8.05 (m, 1H), 7.76-7.62 (m, 3H), 4.22 (d, J=2.5 Hz, 2H), 3.57 (td, J=6.6, 2.9 Hz, 4H), 2.21 (t, J=2.5 Hz, 1H), 2.14-2.06 (m, 2H).

Provenance & Evidence