N-bromobutanimide → 1-Bromo-2-methoxy-4-methyl-5-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

To a solution of nitrobenzene 11 (2.2 g, 13.1 mmol) in CH3CN (8 mL) in a pressure tube was added N-bromosuccinimide (8.2 g, 45.8 mmol). The tube was sealed and the contents were heated to 140° C. overnight on an oil bath. The reaction mixture turned brownish-red overnight. After the reaction was quenched with saturated aqueous Na2S2O3 solution (150 mL), the product was extracted with Et2O (2×150 mL), dried (Na2SO4), and purified by chromatography (hexane/EtOAc 3:1) to afford brominated product 12 along with other byproducts that were not separable by chromatography (hexane/EtOAc 3:1). The product mixture (2.8 g, 87%) was used directly in the next step: Rf0.29 (hexane/EtOAc 3:1); 1H NMR (CDCl3) δ 2.66 (s, 3H), 3.98 (s, 3H), 6.76 (s, 1H), 8.31 (s, 1H); 13C NMR (CDCl3) δ 21.7, 56.8, 108.9, 114.3, 125.2, 130.4, 136.3, 141.9, 159.3; ESI-HRMS [M-Br—CH3—H]− C7H6NO3 calcd for m/z 152.0348, found 152.0349.

Provenance & Evidence