Bromine → HCID 19784796, compound

Participants

Reaction Steps

Bromine (2.33 ml, 2 eq.) in acetic acid (15 ml) was added dropwise to a stirred solution of N-(2,2,2-trifluoroethyl)-2-nitroaniline (4) (5.0 g, 23 mmol) inacetic acid (50 ml), in an ice bath. After the bromine addition was completed, the ice bath was removed and the reaction mixture was stirred at room temperature for 30 minutes and poured onto crushed ice. The resultant yellow-orange precipitate was collected by filtration, washed with H2O three times and air dried to give 6.0 g (88% yield) of N-(2,2,2,-trifluoroethyl)-4-bromo-2-nitroaniline (5): mp 118°-120° C.; MS m/e 298 (M+), 1HNMR (DMSO-d6) δ 4.33 (m, 2H), 7.28 (d, 1H, J=9.0 Hz), 7.72 (dd, 1H, J=2.2 Hz, 9.0 Hz), 8.18 (d, 1H, J=2.1 Hz), 8.31 (1H, -NH).

Provenance & Evidence