Benzoyl Peroxide → HCID 19698387, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-tert-butoxycarbonylmethoxy-4-nitrotoluene (36.1. g, 120 mmol), N-bromosuccinimide (21.3 g, 120 mmol), and benzoyl peroxide (4 g) in carbon tetrachloride (500 mL) was refluxed for 18 h. The insoluble material formed was removed by filtration and the filtrate was concentrated. The residue was dissolved in DMF (10 mL) and sodium azide (5.2 g, 80 mmol) was added. The mixture was stirred for 2 h at 50° C., poured into brine, and extracted with a 1:1 mixture of toluene and ethyl acetate. The organic layers were washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 9:1 to 7:3 hexane/ethyl acetate to give 13.4 g of the title compound (36%): 1H NMR (CDCl3) δ7.89 (d, 1H, J=8.3 Hz), 7.01 (dd, 1H, J=8.3, 1.7 Hz), 6.93 (d, 1H, J= 1.7 Hz), 4.70 (s, 2H), 4.43 (s, 2H), 1.48 (s, 9H).

Provenance & Evidence