4-Chloroanisole → 4-Methoxybiphenyl

Participants

Reaction Steps

According to General Procedure A, a mixture of 4-chloroanisole (0.06 mL, 0.50 mmol), phenylboronic acid (91 mg, 0.75 mmol), CsF (228 mg, 1.50 mmol), Pd(OAc)2 (2 mg, 0.01 mmol) and 12f (8 mg, 0.02 mmol) in 1,4-dioxane (2.5 mL) was heated to reflux, cooled and filtered. Evaporation of the solvent under reduced pressure and column chromatography of the pre-adsorbed crude material (0.5-1.0% isopropanol/hexane, silica gel) gave 51e (64 mg, 70%) as a colorless solid. 1H NMR (300 MHz, CDCl3) δ 7.54 (t, 4H, J=6.8 Hz), 7.42 (t, 2H, J=6.8 Hz), 7.32-7.26 (m, 1H), 6.99 (d, 2H, J=8.7 Hz), 3.86 (s, 3H); 13C NMR (75.5 MHz, CDCl3) δ 159.1, 140.8, 133.8, 128.7, 128.1, 126.7, 126.6, 114.2, 55.3.

Provenance & Evidence