1-Ethynyl-3-methoxybenzene → HCID 58156649, compound

Participants

Reaction Steps

To a solution of 1-ethynyl-3-methoxybenzene (396 mg, 3.00 mmol, Aldrich) in 50% tert-butanol/water (4.0 mL) is added 300 μL (0.30 mmol) of an aqueous solution of sodium ascorbate (594 mg in 3 mL H2O), 100 μL (0.030 mmol) of an aqueous CuSO4.5H2O solution (75 mg in 1 mL H2O), followed by 4-azidobenzoic acid (489 mg, 3 mmol). The resulting mixture is stirred for 7 days, the resulting suspension filtered and washed with H2O (3×30 mL), Et2O (2×15 mL), and hexanes (3×30 mL). The solid is dried overnite in vacuo (70° C., 10 torr) to afford 880 mg (99%) of 4-[4-(3-methoxy-phenyl)-[1,2,3]triazol-1-yl]benzoic acid as a pale yellow powder: m.p. 276-277° C. 1H NMR (300 MHz, DMSO-d6) δ 9.44 (s, 1H), 8.16 (d, J=8.5 Hz, 2H), 8.08 (d, J=8.3 Hz, 2H), 7.52 (m, 2H), 7.40 (t, J=7.8 Hz, 1H), 6.95 (ddd, J=8.3, 2.5, 0.8 Hz, 1H), 3.82 (s, 3H). MS m/z 296.29, calcd for C16H13N3O3 (M+H+) 296.

Provenance & Evidence