Water → HCID 12834670, compound

Participants

Reaction Steps

A mixture of 5-bromo-2-iodobenzaldehyde (3B Scientific Corp., 5.83 g, 18.8 mmol), o-tolylboronic acid (2.55 g, 18.8 mmol), cesium fluoride (8.55 g, 56.4 mmol) and bis(triphenylphosphine)palladium(II) chloride (263 mg, 0.38 mmol) was prepared in dioxane (60 mL) and water (25 mL) under nitrogen atmosphere and was heated at 50° C. for 16 hours. The reaction mixture was cooled at RT, diluted with MTBE (250 mL) and the layers were separated. The organic layer was washed with water (100 mL) and brine (100 mL). The aqueous layers were extracted with MTBE (150 mL). The organic layers were combined, dried (Na2SO4) and concentrated under vacuum. After purification by flash chromatography (silica, hexane/EtOAc), the title compound was obtained as a pale yellow solid (4.63 g, 90%). HPLC (Method A) Rt 5.6 min (Purity: 93%). 1H NMR (DMSO-d6, 300 MHz) δ 9.57 (s, 1H), 8.02 (s, 1H), 7.94 (m, 1H), 7.39-7.27 (m, 4H), 7.20 (m, 1H), 2.06 (s, 3H).

Provenance & Evidence