(3-Methoxyphenyl)boronic acid → HCID 59504489, compound

Participants

Reaction Steps

Dissolve 2-iodo-4,4-dimethyl-cyclohex-2-enone(Tetrahedron Letters (1994), 35(37), 6787-90) (11 g, 44 mmol) in tetrahydrofuran (200 ml). Add 3-methoxyphenyl boronic acid (10 g, 65.8 mmol), triphenyl arsine (808 mg, 2.64 mmol), silver oxide (15.3 g, 66 mmol) in water (25 ml), bis(benzonitrile)dichloropalladium(II) (506 mg, 1.32 mmol). Stir at room temperature for 1 h. Quench with saturated aqueous ammonium chloride (200 ml), and stir 1 h. Filter reaction mixture through a bed of celite rinsing celite with ether (200 ml). Separate filtrate layers and extract the aqueous layer with additional ether (200 ml), combine organic extracts, and wash with water 2×(200 ml), brine (100 ml), dry, and concentrate. Chromatograph residue on a Biotage eluting with 10% ethyl acetate in hexanes to give (10.1 g, 99%) of the title compound as a yellow oil: 1H NMR (CDCl3) δ 7.26-7.23 (m, 1H), 6.88-6.84 (m, 3H), 6.69 (s, 1H), 3.81 (s, 3H), 2.62 (t, 2H), 1.96 (t, 2H), 1.25 (s, 6H).

Provenance & Evidence