Ethanamine, 2,2,2-trifluoro- → HCID 11098529, compound

Participants

Reaction Conditions

Reaction Steps

2,2,2-Trifluoroethylamine (24 g, 242 mmol) was added rapidly to a stirred solution of 4-bromo-3-bromomethylanisole (33.6 g, 120 mmol) in anhydrous DMSO (125 mL) at RT. The reaction warmed to approximately 30-35° C. After stirring for 18 hr, the reaction was diluted with ice-cold 1 N NaOH (200 mL) and extracted with Et2O (2×300 mL). The combined organic layers were washed with brine (300 mL), dried (MgSO4), and concentrated to give the title compound (41.35 g, 96%) as a pale yellow oil: TLC (toluene) Rf 0.32; 1H NMR (400 MHz, CDCl3) δ 7.43 (d, J=9 Hz, 1H), 6.97 (d, J=3 Hz, 1H), 6.71 (dd, 1H), 3.93 (br s, 2H), 3.80 (s, 3H), 3.18 (m, 2H), 1.86 (br s, 1H).

Provenance & Evidence