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-trifluoro- ethyl)-2-nitroaniline (4) (5.0g, 23 mmol) in acetic acid (50 ml), in an ice bath. After the bromine addition was completed, the i-ce 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) δ4.33 (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