Potassium Carbonate → 2-(3-Chloropropoxy)-1-methoxy-4-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-methoxy-5-nitrophenol (16.90 g, 100 mmol), 3-chloropropyl p-toluenesulfonate (29.2 g, 120 mmol) and potassium carbonate (27.0 g, 195 mmol) in 160 mL of N,N-dimethylformamide was heated at 80° C. for 2 hours. The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, dried over magnesium sulfate and filtered. The solution was concentrated in vacuo and recrystallized from hexane and ethyl acetate to give 4.68 g of 2-(3-chloropropoxy)-1-methoxy-4-nitrobenzene as a first crop of off-white crystals. A second crop of 11.10 g was obtained from the mother liquor. The remaining solution was concentrated in vacuo and purified by flash column chromatography, eluting with 4:1 hexane:ethyl acetate, to provide 1.31 g of 2-(3-chloropropoxy)-1-methoxy-4-nitrobenzene as off-white crystals, mp 85-87° C.; 1H NMR (400 MHz, DMSO-d6) δ 2.23 (m, 2H), 3.79 (t, J=6 Hz, 2H), 3.92 (s, 3H), 4.21 (t, J=6 Hz, 2H), 7.19 (d, J=9 Hz, 1H), 7.77 (d, J=2 Hz, 1H), 7.92 (dd, J=9, 2 Hz, 1H); MS (ES) m/z246.1, 248.1 (M+H)+

Provenance & Evidence