Tert-butyl 2-methyl-4-(trifluoromethyl)phenylcarbamate → 4-Amino-3-methylbenzotrifluoride

Participants

Reaction Steps

tert-Butyl 2-methyl-4-(trifluoromethyl)phenylcarbamate (1 1.6 g, 42 mmol) was dissolved in trifluoroacetic acid (17% in dichloromethane, 90 mL) and stirred at room temperature for 30 min. The reaction was concentrated and taken up in water/pentane. The aqueous was neutralized with saturated sodium bicarbonate, and the layers separated. The organics were dried over magnesium sulfate and concentrated to give 7.8 g (quant.). 1H-NMR (CDCl3, 500 MHz) δ 7.25-7.40 (m, 2H), 6.67 (d, J=7.9 Hz, 1H), 3.87 (bs, 2H), 2.18 (s, 3H); 13C-NMR (CDCl3, 126 MHz) δ 147.7, 127.5 (q, J=3.8 Hz), 125.0 (q, J=271 Hz), 124.4 (q, J=3.8 Hz), 120.3 (q, J=33 Hz), 114.1, 17.2. Mass spec.: 176.03 (MH)+.

Provenance & Evidence