Water → 7-Oxocyclohepta-1,3,5-trien-1-yl 4-nitrobenzenesulfonate

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Reaction Steps

2-Hydroxycyclohepta-2,4,6-trienone (0.2 g, 1.7 mmol) was reacted with 4-nitrobenzenesulfonyl chloride (1.1 g, 4.9 mmol) in 5 mL of pyridine. Addition of 10 mL of water allowed for precipitation of PZBG-4c in 71% yield (0.38 g, 1.2 mmol) without the need for further purification. 1H NMR (400 MHz, DMSO) δ=8.45 (d, J=8.8 Hz, 2H), 8.22 (d, J=8.8 Hz, 2H), 7.52 (d, J=9.2 Hz, 1H), 7.46 (dd, J1=10.2 Hz, J2=3.6 Hz, 1H), 7.31 (dd, J1=9.8 Hz, J2=2 Hz, 1H), 7.15 (dd, J1=10.6 Hz, J2=3.6 Hz, 1H). 13C (100 MHz, CDCl3) δ=179.09, 154.86, 151.50, 141.95, 141.27, 138.59, 136.87, 132.06, 131.48, 130.42, 125.42. ESI-MS(+): m/z 308.01 [M+H]+, 324.73 [M+NH4]+

Provenance & Evidence