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

Reaction equation

[F:1][C:2]([F:17])([F:16])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)(=[O:5])=[O:4].[OH-].[Na+]>C(O)C.Cl>[F:16][C:2]([F:1])([F:17])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)(=[O:4])=[O:5]

Participants

Procedure

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: