Hydrochloric Acid → HCID 67202556, compound

Participants

Reaction Steps

2.1 mL of BBr3 solution (5.56 g, 22.2 mmol) was added dropwise into a solution of 15f (1.23 g, 1.76 mmol) in 60 mL of anhydrous CH2Cl2 at −78° C. Stirring was continued at −78° C. for 1 h, 0° C. for 1 h, and ambient temperature for 1 h, respectively. 300 grams of ice containing 30 mL of 6M HCl was added to the mixture and stirred for 0.5 h at room temperature. The aqueous layer was extracted with dichloromethane (3×100 mL). The combined organic layer was washed with water, brine and dried over MgSO4. The solvent was concentrated in vacuo and the residue was purified by C-18 column chromatography (H2O/Acetonitrile) to give 1.1 g of compound 2f (90%) as white solid. Yield, 45%; NMR (600 MHz, CD3OD) δ 7.45 (s, 2H), 7.34 (s, 2H), 7.20 (d, J=7.2 Hz, 4H), 7.08 (d, J=7.2 Hz, 4H), 3.27 (m, 4H), 2.87 (m, 4H), 2.31 (s, 6H), 2.03 (s, 6H). HPLC purity 96.6%, tR=17.00 min (Method A). HRMS calcd for C40H38O6 615.2741 (M+H). found 615.2720.

Provenance & Evidence