Ethyl Acetate → N-{4-[(6-hydroxy-3-methyl-2-phenyl-1-naphthalenyl)oxy]phenyl}methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

A stirring solution of 269 (0.27 g, 0.62 mmol) in CH2Cl2 (10 mL) chilled to −20° C. under N2 was added BBr3 (0.47 g, 1.86 mmol), dropwise, via syringe, over 1 minute. The resulting yellow/orange r×n was stirred for 2 h at −20° C. and then poured over 50 g ice followed by addition of EtOAc (50 mL). The resulting slurry was transferred to a separatory funnel and the organic layer washed with brine (50 mL), dried (Na2SO4) and concentrated to a pale yellow foam. The crude product was purified by silica gel column chromatography with 2% MeOH: CH2Cl2 to yield 162 mg (63%) of the title compound 270, as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 2.13 (s, 3H), 2.83 (s, 3H), 6.55 (d, J=9.0 Hz, 2H), 6.97 (d, J=8.3 Hz, 2H), 6.96 (dd, J1=2.3 Hz, J2=9.1 Hz, 1H), 7.12 (d, J=2.3 Hz, 1H), 7.16 (d, J=7.0 Hz, 1H), 7.21-7.30 (m, 4H), 7.54 (d, J=8.5 Hz, 1H), 7.55 (s, 1H), 9.33 (s, 1H), 9.84 (s, 1H). Anal. Calc for C29H26O3.0.5H2O: C, 67.27; H, 5.18; N, 3.27. Found: C, 67.13; H, 5.04; N, 3.27.

Provenance & Evidence