Nitrogen → 4-(4-TRIFLUOROMETHYLPHENYL)BENZYLAMINE

Participants

Reaction Conditions

Reaction Steps

To a nitrogen purged flask containing 4-trifluoromethylphenyl boronic acid (76.6 g, 403 mmol), [1,1′-bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) (6.07 g, 9.31 mmol), and potassium carbonate (83.6 g, 605 mmol) were added 4-bromobenzylamine (75.0 g, 403 mmol), N2 sparged 2-methyltetrahydrofuran (750 mL) and N2 sparged water (750 mL). The mixture was then warmed to 80° Celsius for 15 h. The mixture was cooled to RT, the layers were separated and the organic layer was washed with brine, dried over magnesium sulfate and filtered through celite. The filtrate was concentrated to dryness to afford the title compound (114.37 g, 85% purity, 96%). MS (ESI): mass calcd. for C14H12F3N, 251.10; m/z found, 252.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.68 (s, 4H), 7.58 (d, J=7.9, 2H), 7.42 (d, J=7.9, 2H) 3.94 (s, 2H). Absolute stereochemistry was determined by alternative synthesis starting with the product of Example 2.

Provenance & Evidence