Water → HCID 11845474, compound

Participants

Reaction Steps

Bromine (0.049 mL, 0.962 mmol) was added dropwise over 5 minutes to a stirring solution of 39 (0.200 g, 0.802 mmol) in acetic acid (2.5 mL). When the reaction was judged complete by HPLC (30 min), H2O was added, and the solid that precipitated was filtered off and washed with H2O. The light purple solid that was obtained was dissolved in EtOAc, washed with Na2SO3 and H2O, then dried with Na2SO4, filtered, and concentrated. The product was purified by preparative reverse phase HPLC with 40:60 H2O:CH3CN (w/0.05% TFA); 20 mL/min.; λ=214 nM. 0.1520 g (57.7%) of 70 was obtained as a fluffy white solid. 1H (CD3OD, 400 MHz): δ 7.22 (2H, d, J=8.8 Hz), 7.12 (2H, d, J=8.8 Hz), 6.65 (1H, s), 2.81 (2H, t, J=7.3 Hz), 2.67 (2H, t, J=7.3 Hz) ppm. Partial 13C (CD3OD, 100 MHz): δ 163.33, 141.42, 132.54, 131.03, 129.18, 124.73, 117.15, 105.84, 36.72, 29.04 ppm. DEPT (CD3OD, 100 MHz): CH2 carbons: 36.72, 29.04; CH carbons: 131.03, 129.18, 117.15 ppm. HPLC: 10.484 min.

Provenance & Evidence