4-Fluorobenzyl chloride → 1-[(4-fluorophenyl)methyl]benzotriazole

Participants

Reaction Steps

In a procedure as in Example 2 but using 1H-benzotriazole (23.8 g, 0.200 mol), 1-(chloromethyl)-4-fluorobenzene (29.0 g,0.200 mol) and K2CO3 (70 g) in CH3CN (300 mL) for 1 hour gave the title compound and (4-fluorophenyl)methyl-2H-benzotriazole. Workup and recrystallization gave the mixture of the 1H and 2H-isomers (75% yield) which was used in the subsequent reactions. A sample (5 g) was chromatographed (PE/EtOAc 9:1) eluting first the 2H isomer and then the title compound: mp 92°-94° C. (cyclohexane); 1H NMR (300 MHz, CDCl3) δ5.82 (s, 2H, CH2), 7.00-7.06 (m, 2H), 7.25-7.46 (m, 5H), 8.08 (d, J=8.9 Hz, 1H); IR (CDCl3) 3052 (w), 2938 (w), 1609, 1513, 1451 (w), 1351 (w), 1315 (w), 1269 (w), 1230 (s), 1159, 1084 cm-1. MS (EI) m/e 227 (M+, 52.6), 198 (100), 109 (96.9); Anal. Calcd for C13H10N3F (227.24): C, 68.71; H, 4.44; F, 8.36; N, 18.49; Found: C, 68.44; H. 4.44; F, 8.40; N, 18.57.

Provenance & Evidence