Iodoethane → 2-Ethoxy-1-methoxy-4-nitro-benzene

Participants

Reaction Steps

Under an inert atmosphere at 0° C., add a solution of 10 g (59 mmol) of 2-ethoxy-5-nitrophenol dissolved in 125 ml of DMF, on a solution of 2.6 g (65 mmol) of 60% NaH in oil dissolved in 125 ml of DMF. After 30 minutes at room temperature, add dropwise 5.2 ml (65 mmol) of EtI at 0° C. Allow to stand at room temperature for 12 hours. Add 1.5 l of a water-ice mixture. Filter the precipitate and wash three times with 100 ml of water then once with 100 ml of pentane. One obtains 9.8 g of the abovenamed product in the form of a white powder. Yield: 93%. 1H-NMR (CDCl3, 300 MHz): d 1.52 (t, 3H, —CH3), 3.98 (s, 3H, OCH3), 4.20 (q, 2H, OCH2), 6.91 (d, 1H Ar), 7.75 (d, 1H Ar), 7.91 (dd,1H Ar).

Provenance & Evidence