3-(Trifluoromethyl)phenol → 8-Nitro-4-(3-(trifluoromethyl)phenoxy)quinazoline

Participants

Reaction Steps

To a solution of 3-(trifluoromethyl)phenol (726 mg, 4.48 mmol) in THF (2 mL) was added NaH (179 mg, 4.48 mmol, 60% in mineral oil) at 0° C. and the reaction mixture was stirred for 15 min. Then a solution of 4-chloro-8-nitroquinazoline (Intermediate-7, step 2, 470 mg, 2.24 mmol) in THF (3 mL) was added to the reaction mixture at the same temperature and the reaction mixture was stirred at rt for 4 h. Then the reaction mixture was quenched with 1N HCl at 0° C. and the precipitate obtained was filtered and purified by column chromatography using 5-10% EtOAc in petroleum ether to afford 430 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.88 (s, 1H), 8.68 (d, J=7.8 Hz, 1H), 8.60 (d, J=7.2 Hz, 1H), 7.99-7.94 (t, J=8.4 Hz, 1H), 7.89 (s, 1H), 7.77 (s, 3H); MS (m/z): 336.12 (M+H)+.

Provenance & Evidence