Sodium Hydroxide → 5-Chloro-1-(4-methoxybenzyl)-1H-1,2,3-benzotriazol-4-ol

참여 물질

반응 단계

To a stirred solution of 1-(4-methoxybenzyl)-1H-1,2,3-benzotriazol-4-ol (0.984 g, 3.85 mmol) at 0° C. in THF (15 mL) was added 1N NaOH (3.85 mL, 3.85 mmol). The resulting mixture was then stirred for several minutes, after which N-chloro-succinimide (0.515 g, 3.85 mmol) was added in one portion. The stirred reaction mixture was quenched after 5 minutes at 0° C. with aqueous ammonium chloride (25 mL) and extracted with dichloromethane (2×100 mL). The combined extracts were concentrated under reduced pressure. The resulting residue was subjected to reverse phase chromatography (5-95% MeCN/H2O, 0.1% TFA). The product fractions were combined and extracted with dichloromethane (2×100 mL). The combined extracts were dried over MgSO4, filtered and concentrated under reduced pressure to afford the title product. 1H NMR (DMSO d6) δ 11.61 (s, 1H), 7.44 (d, J=8.5 Hz, 1H), 7.30 (d, J=8.5 Hz, 2H), 7.23 (d, J=8.6 Hz, 1H), 6.90 (d, J=8.8 Hz, 2H), 5.84 (s, 2H), 3.71 (s, 3H).

출처 및 근거