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 (2X). Evaporation provided 1.6 g of 4-nitro-3-methoxymethylchlorobenzene. 1H-NMR (500 MHz, CDC13) 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