Sodium Hydroxide → Methanesulfonic acid, trifluoro-, 4-aminophenyl ester

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Reaction Steps

The 4-(trifluoromethylsulfonyloxy)-1-nitrobenzene (27.1 grams; 0.10 mole) in 300 ml of ethanol was added dropwise to 94.8 grams of stannous chloride (0.5 mol; 5 equivalents) in 525 ml of concentrated HCl, at room temperature. The rate of addition was controlled to prevent the temperature of the reaction mixture from rising. The reaction mixture was stirred for 3 hours, 10N NaOH added until the pH was ~12, and extracted into ether. The ether extract was washed with water, dried over magnesium sulfate, and the ether evaporated to yield the desired 4-(trifluoromethylsulfonyloxy)aniline as a yellowish brown oil. Its identity was confirmed by NMR, MS, and elemental analysis, the last of which showed:

Provenance & Evidence