Hydrochloric Acid → HCID 57882765, compound

Participants

Reaction Conditions

Reaction Steps

2-Bromo-6-(trifluoromethoxy)naphthalene (428 mg, 1.47 mmol), bis(pinacolato)diboron (410 mg, 1.62 mmol), and KOAc (433 mg, 4.41 mmol) were suspended in DMSO (12 ml). The mixture was de-oxygenated by vacuum-N2 fill cycles, followed by the addition of catalyst PdCl2(dppf) (30 mg, 2.5 mol %). The reaction was heated under N2 atmosphere to 80° C. for 2 hr. The reaction was diluted with hexane (100 ml), washed with water, brine, and dried over Na2SO4. After evaporation of solvent, the residue obtained was treated with acetone (20 ml) and 2N HCl (5 ml) for 24 h. The crude boronic acid was purified by reverse phase HPLC to give [6-(trifluoromethoxy)-2-naphthyl]boronic acid as a white powder. NMR (500 MHz, CDCl3) δ: 7.44 (dd, J=2.3, 9.0 Hz, 1H); 7.74 (br s, 1H); 7.98 (d, J=8.2 Hz, 1H); 8.11 (d, J=9.0 Hz, 1H); 8.35 (dd, J=1.1, 8.2 Hz, 1H); 8.85 (br s, 1H).

Provenance & Evidence