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

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Reaction Steps

To a stirring solution of 273 (0.14 g, 0.31 mmol) in CH2Cl2 (6 mL), chilled to −20° C. under N2, was added BBr3 (0.24 g, 0.94 mmol) dropwise, via syringe, over 1 minute. After 90 min at −20° C. the r×n was poured over 50 g ice followed by EtOAc (50 mL). The EtOAC layer was washed with brine (50 mL), dried (Na2SO4) and concentrated to a viscous yellow oil that was purified by column chromatography using a gradient of 100% CH2Cl2 to 1% MeOH: CH2Cl2 to yield a foam. The foam was crystallized from EtOAc/hexanes to yield the title compound 274, as a light yellow solid (72 mg, 55%). 1H NMR (400 MHz, DMSO-d6): δ 2.13 (s, 3H), 4.33 (q, J=9.8 Hz, 2H), 6.57 (d, J=9.0 Hz, 2H), 6.96 (d, J=9.0 Hz, 2H), 6.97 (dd, J1=2.4 Hz, J2=9.1 Hz, 1H), 7.12-7.30 (m, 5H), 7.53 (s, 1H), 7.55 (d, J=9.8 Hz, 1H), 9.40 (s, 1H), 9.84 (s, 1H), 10.06 (s, 1H).

Provenance & Evidence