Pyrazole → 1-(4-Methoxyphenyl)-1H-pyrazole

Participants

Reaction Steps

1-(4-Methoxyphenyl)-1H-pyrazole was prepared as described in the literature (Tetrahedron Lett. 39 (1998) 2941-2944). To pyrazole (1.0 g, 14.7 mmol) dissolved in a reaction vessel containing CH2Cl2 (100 mL) and 4 Å molecular sieves (6.0 g) was added 4-methoxyphenylboronic acid (4.5 g, 29.4 mmol), pyridine (3 mL, 36.7 mmol) and copper (II) acetate (4.0 g, 22.0 mmol). The reaction mixture was stirred at room temperature for 72 h and then filtered through a plug of Celite. The filtrate was concentrated in vacuo and then purified by flash chromatography (SiO2, EtOAc/hexane, 1:9, then 1:4) to afford a clear oil in 47% yield.

Provenance & Evidence