4-Nitrotoluene → o-Toluenesulfonyl chloride, 5-nitro-

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Reaction Steps

Chlorosulfonic acid (50 mL, 750 mmol) was added within about 30 min dropwise to a solution of p-nitrotoluene (13.7 g, 100 mmol) in CHCl3 (50 mL) under ice cooling. After addition, the mixture was refluxed for about 6 h, cooled, the mixture poured into ice water (500 mL) and extracted with CHCl3 (3×300 mL). The CHCl3 layer was washed with water (2×200 mL) and dried with Na2SO4. Evaporation of CHCl3 gave 5-nitro-2-methyl-phenylsulfonyl chloride (18.4 g, 78%): 1H NMR (DMSO-d6) δ: 8.92 (d, J=2.4 Hz, 1H), 8.46 (dd, J=2.4 Hz, 1H), 7.66 (s, 1H), 2.92 (s, 3H).

Provenance & Evidence