Phenylboronic Acid → HCID 23445658, compound

Participants

Reaction Conditions

Reaction Steps

At ambient temperature, to a stirred mixture containing phenylboronic acid (0.454 g, 3.73 mmol), barium hydroxide octahydrate (1.60 g, 5.08 mmol) and palladium (II) acetate (7.60 mg, 0.0339 mmol) in DME:H2O (6:1, 20 mL) was added a solution of 2-n-butyl-3-(4-[(2-methoxyethoxy)methoxy]-3,5-diiodobenzoyl)benzofuran (1.07 g, 1.69 mmol) in DME:H2O (6:1, 20 mL). After the addition was complete, the reaction was heated at 80° C. for 16 h. The reaction was cooled to ambient temperature, diluted with ether (50 mL), washed sequentially with sat. aq. NaHCO3 (3×), with brine (3×), dried (MgSO4) and concentrated. The crude product was purified on Biotage KP-Sil eluting with 25% ether/pet. ether to give 0.380 g (42%) of the title compound. 1H NMR (DMSO-d6) δ 0.76 (t, 3H), 1.22 (sextet, 2H), 1.64 (quintet, 2H), 2.81-2.92 (m, 6H), 3.03 (s, 3H), 4.44 (s, 2H), 7.31-7.67 (m, 14H), 7.76 (s, 2H).

Provenance & Evidence