Carbon tetrabromide → HCID 69475736, compound

Participants

Reaction Steps

To a solution of compound 3 (0.12 g, 0.27 mmol) and CBr4 (0.11 g, 0.33 mmol) in 5.0 mL of anhydrous CH2Cl2 was added PPh3 (0.12 g, 0.41 mmol) at 0° C. under N2 atmosphere. The resulting solution was stirred for 48 h at room temperature. The solvent was removed under reduced pressure and the residue was purified on silica gel column chromatography (Hexane:EtOAc=1:2 to 1:4 v/v) to give compound 4 (0.08 g, 0.16 mmol) in 60% yield. 1H NMR (CDCl3, 400 MHz) δ 8.95 (br, 1H), 8.14 (d, J=7.6, 1H), 8.05 (d, J=7.2, 2H), 7.92 (d, J=7.2, 2H), 7.62 (m, 3H), 7.52 (d, J=7.6, 1H), 7.48 (m, 3H), 6.06 (dd, J=15.2, 1.2, 1H), 5.63 (dd, J=4.8, 1.2, 0.5H), 5.50 (dd, J=4.8, 1.2, 0.5H), 5.44 (m, 1H), 4.68 (m, 1H), 3.92 (dd, J=12.0, 4.0, 1H), 3.77 (dd, J=12.0, 4.8, 1H); MS calcd for C23H19BrFN3O5 m/z 516.1 (M+H)+, found 518.3.

Provenance & Evidence