O-Phenylenediamine → HCID 89418652, compound

Participants

Reaction Steps

Benzene-1,2-diamine (4.83 g, 44.6 mmol) was dissolved in hexafluoroisopropanol (9.37 mL, 89 mmol), (R)-trifluoromethylepoxide (0.769 mL, 8.92 mmol) was added, and the resulting reaction mixture was stirred at room temperature for 4 hours. The solution was concentrated and purified on a silica gel column with a 0-100% EtOAc/Hexanes gradient in a 100 g cartridge. (R)-3-[(2-aminophenyl)amino]-1,1,1-trifluoropropan-2-ol (1.30 g, 5.90 mmol) was obtained in 66.2% yield. 1H NMR (400 MHz, CDCl3) 83.32 (dd, J=13.4, 8.3 Hz, 1H), 3.55 (dd, J=13.5, 3.3 Hz, 1H), 3.55 (bs, 3H), 4.22 (m, 1H), 6.71 (d, J=7.7 Hz, 1H), 6.79 (m, 2H), 6.87 (d, d, J=7.7, 2.2 Hz, 1H). MS m/z=221.00

Provenance & Evidence