2-Fluoroethyl bromide → 1-(2-Fluoroethyl)-4-[3-(methyloxy)-4-nitrophenyl]pyridinium bromide

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Reaction Conditions

Reaction Steps

To 4-[3-(methyloxy)-4-nitrophenyl]pyridine (Example 137, step A) (2.3 g, 10 mmol) in pinacolone (25 mL) is added 1-bromo-2-fluoroethane (2.5 g, 20 mmol). The mixture was stirred at 110° C. in a sealed tube overnight. The solution was cooled to rt and the solid collected by vacuum filtration washing with acetone. The title compound of step A (2.0 g, 5.6 mmol, 56%) was obtained as a beige solid. 1H NMR (400 MHz, DMSO-d6) δ9.21 (d, J=7.0 Hz, 2H), 8.68 (d, J=7.3 Hz, 2H), 8.12 (d, J=8.4 Hz, 1H), 7.92 (d, J=1.8 Hz, 1H), 7.77 (dd, J=8.4, 1.8 Hz, 1H), 5.05 (s, 2H), 5.00-4.90 (m, 2H), 4.07 (s, 3H). MS (ESI) m/z=277 [M].

Provenance & Evidence