Dimethyl Sulfate → 2-[1-(Methanesulfonyl)ethyl]-6-(trifluoromethyl)aniline

Participants

Reaction Steps

A mixture of 50% NaOH (50 mL), CH2Cl2 (50 mL), triethylbenzylammonium chloride (30 mg), Me2SO4 (2.50 mL, 26.41 mmol) and 2-methylsulfonylmethyl-6-trifluoromethyl nitrobenzene 3 (6.8 g, 24.01 mmol) was stirred rapidly for 30 min. The mixture was poured onto ice/water (400 mL) and the organic layer separated. The solvent was removed and excess Me2SO4 removed at 60° C. and 0.7 mm, to give a yellow solid which was identified as the same product as in Example 2, i.e., 2-(1-methylsulfonylethyl)-6-trifluoromethyl nitrobenzene. The solid was transferred to a Parr bomb with EtOAc/EtOH (2:1, 100 mL, not all soluble). Five drops of acetic acid and Pd/carbon was added. The mixture was hydrogenated at 60° C. and 60 psi H2 for 15 hrs. The mixture was filtered and the solvent removed to give a brown solid. Washing with ether gave 4.03 g (15.07 mmol, 62.8%) of 2-(1-methylsulfonylethyl)-6-trifluoromethyl aniline as a white solid, mp 153°-5° C.

Provenance & Evidence