Sodium Iodide → 6-Bromo-1-(2-iodoethyl)-1,2,3,4-tetrahydroquinoline

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Reaction Steps

A suspension of 6-bromo-1-(2-chloroethyl)-1,2,3,4-tetrahydroquinoline (compound 2, 1.80 g, 6.56 mmol) and sodium iodide (9.83 g, 65.6 mmol) in acetone (50 mL) was heated to reflux for 2 days at which time TLC analysis showed residual starting material 2. At this time a further portion of sodium iodide (19.66 g, 132.0 mmol) was added and the suspension refluxed for 5 days. The mixture was cooled to room temperature, filtered through a pad of celite and the filtrate concentrated to yield a yellow solid. The solid was taken up in a mixture of ethyl acetate/hexanes (150 mL) and filtered through a pad of silica gel, and the pad rinsed further with EtOAc/Hexanes. The filtrate was concentrated to yield a yellow oil, 3 (2.19 g, 91%). 1H-NMR (CDCl3) δ 7.12 (dd, 1H, J=8.7, 2.5 Hz), 7.09-7.04 (m, 1H), 6.42 (d, 1H, J=8.7), 3.65-3.60 (m, 2H), 3.33 (t, 2H, J=5.6 Hz), 3.25-3.19 (m, 2H), 2.72 (t, 2H, J=6.3 Hz), 1.98-1.90 (m, 2H). MS (ESI+): 366/368 (MH+, 100).

Provenance & Evidence