Pentamethylbenzene → 9-(4-(tert-Butyl)pyridin-2-yl)-9H-carbazol-2-ol

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(benzyloxy)-9-(4-tert-butylpyridin-2-yl)-9H-carbazole 9 (3.00 g, 7.38 mmol, 1.0 eq) and pentamethylbenzene (3.33 g, 22.14 mmol, 3.0 eq) in dichloromethane (74 mL) was cooled to −78° C. in a dry ice-acetone bath, then BCl3 (18.45 mL, 18.45 mmol, 1.0 M in dichloromethane) was added dropwise. After that, the mixture was stirred at −78° C. for 30 minutes, then quenched with methanol. The dry ice-acetone bath was removed and the mixture was warmed to room temperature. The pH of the solution was adjusted to about 6-7 using Et3N, then the solution was washed with saturated NaHCO3 solution until there was no gas to generate, dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the residue was purified through column chromatography on silica gel using hexane/ethyl acetate (10:1-3:1) first, then dichloromethane/methanol (10:1) as an eluent to obtain the desired product, 9-(4-tert-butylpyridin-2-yl)-9H-carbazol-2-ol 10, as a grey solid (2.27 g in 97% yield). 1H NMR (DMSO-d6, 400 MHz): δ 1.40 (s, 9H), 6.79 (dd, J=8.0, 2.0 Hz, 1H), 7.15 (d, J=2.0 Hz, 1H), 7.25 (t, J=7.2 Hz, 1H), 7.32-7.36 (m, 1H), 7.50 (dd, J=5.6, 1.6 Hz, 1H), 7.65 (d, J=2.0 Hz, 1H), 7.68 (d, J=8.4 Hz, 1H), 8.00 (d, J=8.4 Hz, 1H), 8.07 (d, J=7.6 Hz, 1H), 8.63 (d, J=5.6 Hz, 1H), 9.62 (s, 1H).

Provenance & Evidence