1-Butanol → 4,7-Bis(4-isobutoxyphenyl)-2-(4-aminophenyl)-2H-benzo[d][1,2,3]triazole

Participants

Reaction Conditions

Reaction Steps

A mixture of Intermediate H (3.98 g, 10.0 mmol), 4-isobutoxyphenylboronic acid (5.00 g, 25.7 mmol), sodium carbonate (5.30 g, 50 mmol) in water (40 mL), tetrakis(triphenylphosphine)palladium(0) (2.00 g), n-butanol (60 mL), and toluene (30 mL) was stirred under argon and heated at 100° C. for 4 hours. The reaction mixture was poured into water (200 mL), stirred for 30 minutes and extracted with toluene (500 mL). The extract was washed with water (200 mL), concentrated to a volume of 100 mL and diluted with dichloromethane (200 mL) and methanol (200 mL). The obtained solution was hydrogenated for 20 minutes at 50 psi over 10% Pd/C (2 g), filtered through a layer of Celite, and the solvent was removed under reduced pressure. The residue was chromatographed (silica gel, hexane/dichloromethane/ethyl acetate, 35:50:5) to give 4,7-Bis(4-isobutoxyphenyl)-2-(4-aminophenyl)-2H-benzo[d][1,2,3]triazole (Intermediate I) (3.80 g, 75%). 1H NMR (400 MHz, CDCl3): δ 8.22 (d, J=8.4 Hz, 2H, 4-aminophenyl), 8.09 (d, J=8.7 Hz, 4H, 4-i-BuOC6H4), 7.57 (s, 2H, benzotriazole), 7.06 (d, J=8.7 Hz, 4H, 4-i-BuOC6H4), 6.79 (d, J=8.5 Hz, 2H, 4-aminophenyl), 3.90 (bs, 2H, NH2), 3.81 (d, J=6.6 Hz, 4H, i-BuO), 2.14 (m, 2H, i-BuO), 1.06 (d, J=7.0 Hz, 12H, i-BuO).

Provenance & Evidence