Boron tribromide → HCID 178425445, compound

Participants

Reaction Steps

Reaction of 165b (0.10 g, 0.271 mmol) and 1M BBr3 (0.33 mL) in CH2Cl2 (8 mL) within 48 h as described for the synthesis of 148a gave compound 167b (0.053 g, 56%) as olive green solid. 1H NMR (400 MHz, CD3OD) δ 8.20 (s, 1H), 7.61 (s, 1H), 7.55 (m, 2H), 7.26 (t, J=7.6 Hz, 1H), 7.12 (d, J=7.5 Hz, 1H), 6.92 (m, 2H), 4.55 (m, 2H), 4.44 (t, J=6.7 Hz, 2H), 2.36 (s, 3H), 2.01 (m, 4H), 1.41 (m, 2H). 13C NMR (100 MHz, CD3OD) δ 149.29, 140.05, 131.87, 131.78, 130.38, 130.20, 127.90, 127.63, 124.13, 122.51, 51.40, 31.07, 30.93, 28.97, 24.49, 22.02. HRMS (EI) calcd for C19H22N4OS [M]+ 354.151. found 354.1523.

Provenance & Evidence