Boron tribromide → HCID 68815056, compound

Participants

Reaction Steps

The desired product was prepared using a procedure similar to step 4 of example 3. Thus, 1-benzyl-4-(4-methoxy-phenyl)-3-methyl-2-phenyl-1H-indole (1.029 g, 2.550 mmol) was reacted with BBr3 (3.1 ml of a 1M solution in CH2Cl2) to give the product (0.657 g, 1.687 mmol, 66%) as a white solid, mp 174-176° C. 1H NMR (DMSO-d6) δ 1.73 (s, 3H), 5.28 (s, 2H), 6.79-6.82 (m, 3H), 6.88 (d, J=7.2 Hz, 2H), 7.07-7.10 (m, 1H), 7.15-7.19 (m, 1H), 7.20-7.23 (m, 4H), 7.28 (dd, J=0.8, 8.3 Hz, 1H), 7.32-7.34 (m, 2H), 7.39-7.47 (m, 3H), 9.41 (s, 1H); IR (solid) 3450, 3050, 1600, 1520, 1420, 1310, 1200 and 1180 cm−1; [ESI(+)], m/z 390 (M+H)+; Anal. Calcd. for C28H23NO: C, 86.34; H, 5.95; N, 3.60; Found: C, 86.13; H, 5.98; N, 3.56.

Provenance & Evidence