1-Bromo-2-Chloroethane → 1-(2-chloroethoxy)-3-nitrobenzene

Participants

Reaction Steps

To a mixture of 3-nitrophenol (5.0 g, 36 mmol) and K2CO3 (7.45 g, 54 mmol), in 2-butanone at 85° C. was added 1-bromo-2-chloroethane (1.7 mL, 71.9 mmol) and the reaction stirred for 24 h. The mixture was cooled to rt and reduced in vacuo. The crude was diluted with EtOAc (200 mL) and water (200 mL) and separated. The aqueous layer was extracted twice with EtOAc (200 mL), the organics were pooled, dried over MgSO4 and reduced in vacuo onto silica gel. Purification was achieved via column chromatography using a gradient of EtOAc/Hexanes to afford a yellow oil that solidified upon standing to afford 4.22 g (58% yield) of titled product as an off-white solid. 1H NMR (400 MHz, DMSO-D6) δ ppm 7.8 (m, 1H), 7.7 (t, J=2.4 Hz, 1H), 7.6 (t, J=8.2 Hz, 1H) 7.4 (dd, J=8.2, 2.6 Hz, 1H), 4.4 (m, 2H), 4.0 (m, 2H).

Provenance & Evidence