(2H-1,3-benzodioxol-5-yl)boronic acid → HCID 69583773, compound

Participants

Reaction Steps

To a solution of ethyl 6-[4,5-methylenedioxyphenyl]-2-naphthoate (19.61 g, 56.50 mmol, prepared in a similar manner via a Suzuki coupling of 3,4-methylenedioxyphenyl boronic acid and 6-carboethoxynaphthyl-2-trifluoromethanesulfonate, 84% yield) in CH2Cl2 (900 mL) was pyridinium tribromide (19.91 g, 62.26 mmol) at RT. The resulting mixture was allowed to stir overnight. After 24 hours, additional amount of pyridinium tribromide (9.05 g, 28.3 mmol) was added and the mixture stirred overnight. The mixture was washed with H2O, brine and dried over magnesium sulfate. After filtering, the solvent was removed and purified on silica gel (CH2Cl2) to give ethyl 6-[3-bromo-4,5-methylenedioxyphenyl]-2-naphthoate (100%) as a white solid. 1H NMR (300 MHz; CDCl3): δ 1.47 (t, J=7.2 Hz, 3H), 4.46 (q, J=7.2 Hz, 2H), 6.05 (s, 2H), 6.90 (s, 1H), 7.15 (s, 1H), 7.57 (dd, J1=9.0 Hz, J2=1.5 Hz, 1H), 7.84 (s, 1H), 7.90 (d, J=9.0 Hz, 1H), 7.98 (d, J=9.0 Hz, 1H), 8.64 (s, 1H).

Provenance & Evidence