(Diethylamino)sulfur trifluoride → 2-Bromo-1-(2-fluoroethoxy)-4-nitrobenzene

Participants

Reaction Steps

To a cooled (-78° C.) suspension of 3-Bromo-4-(2-hydroxy)ethoxy nitrobenzene (7.9 g, 30 mmol) in dichoromethane (80 ml) was added diethylaminosulphur trifluoride (3.88 ml, 31.5 mmol). The solution was stirred at ambient temperature for 2 hours, then quenched by the dropwise addition of water (100 ml). The organic layer was separated, washed with brine (100 ml), dried (MgSO4), and evaporated in vacuo. Purification on silica, eluting with 15%-20% ethyl acetate in hexane afforded the title compound as a yellow oil (1.2 g, 15%). 1H NMR (250 MHz, CDCl3) δ 4.35 (1H, dd, J=4.1 Hz, J=2.4 Hz), 4.45 (1H, dd, J=2.4 Hz, J=4.1 Hz), 4.75 (1H, dd, J=4 Hz, J=5.8 Hz), 4.95 (1H, dd, J=4 Hz, J=5.8 Hz), 6.98 (1H, d, J=9.1 Hz), 8.21 (1H, dd, J=2.7 Hz, J=9 Hz).

Provenance & Evidence