Sodium Methoxide → 4-Chloro-2-(methoxymethyl)-1-nitrobenzene

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Reaction Steps

2.15 g of 5-chloro-2-nitrobenzylbromide is dissolved in approximately 25 ml methanol at room temperature. 1.86 g of 25% sodium methoxide in methanol is added and stirring continued for 0° C. 1 hour after which 10 wt % additional sodium methoxide is added to complete the conversion. The solvent is evaporated and the residue is dissolved in 100 ml dichloromethane and washed with 25 ml water (2×). Evaporation provided 1.6 g of 4-nitro-3-methoxymethylchlorobenzene. 1H-NMR (500 MHz, CDCl3) δ (ppm) 3.527 (s, 3H), 4.838 (s, 2H), 7.399-7.416 (dd, 1H), 7.824-7.826 (d, 1H), 8.066-8.084 (d, 1H).

Provenance & Evidence