Hydrochloric Acid → HCID 16203219, compound

Participants

Reaction Steps

To a solution of (175) (0.100 g, 0.28 mmol) under an argon atmosphere in dichloromethane (5 mL) was added BBr3 (1.0 mL, 1.0 M solution in dichloromethane) at −78° C. The reaction mixture was stirred at room temperature for 1 h and then poured into an ice cold solution of HCl (1.0 N). The mixture was extracted in ethyl acetate. The organic layer was washed with water, dried over anhydrous Na2SO4, filtered and concentrated. The solid obtained was recrystallized from ethyl acetate to give (176): (62 mg, 67%): mp 164-67° C., 1H NMR (400 MHz, DMSO-CDCl3): δ 0.70-0.90 (m, 1H), 1.41-1.46 (m, 1H), 2.41-2.57 (m, 5H), 3.15-3.22 (m, 1H), 5.29 (d, J=11.2 Hz, 1H), 6.43 (d, J=6.8 Hz, 2H), 6.53-6.57 (m, 3H), 6.68 (d, J=8.4 Hz, 1H), 7.19 (s, 1H). HFABMS m/z 323.1399 (calc for C19H18N2O3, MH+, 323.1396).

Provenance & Evidence