Pyridine → 3,5-Dichloro-4-(4-methoxyphenoxy)benzyl Alcohol

Participants

Reaction Steps

To a flask containing 24 ml of dichloromethane was added 4 A sieves (2.97 g, activated at 500° C. for 8 h), 4-methoxyphenylboronic acid (1.84 g, 12.0 mmol), 2,6-dichloro-4-hydroxymethylphenol (465 mg, 2.41 mmol), copper (II) acetate (438 mg, 2.41 mmol), pyridine (0.97 ml, 12.0 mmol) and triethylamine (1.67 ml, 12.0 mmol). The reaction flask was fitted with a drying tube and stirred overnight. Filtration through celite and removal of volatiles in vacuo followed by column chromatography (silica, 30% ethyl acetate in hexane) provided the title compound as light brown oil (323 mg, 44%). 1H NMR (400 MHz, CDCl3) δ 7.39 (s, 2H), 6.82 (d, j=7.2 Hz, 2H), 6.77 (d, j=7.2 Hz, 2H), 4.69 (s, 2H), 3.76 (s, 3H).

Provenance & Evidence