Boron tribromide → HCID 68815835, compound

Participants

Reaction Steps

The desired product was prepared using a procedure similar to step 4 of example 3. Thus, 5-(4-methoxy-phenyl)-1,3-dimethyl-2-phenyl-1H-indole (0.560 g, 1.710 mmol) was reacted with BBr3 (2.1 ml of a 1M solution in CH2Cl2) to give the desired product (0.484 g, 1.544 mmol, 90%) as a white solid, mp 148-150° C. 1H NMR (DMSO-d6) δ 2.24 (s, 3H), 3.60 (s, 3H), 6.84 (d, J=8.6 Hz, 2H), 7.40 (dd, J=1.4, 8.4 Hz, 1H), 7.44-7.47 (m, 4H), 7.50-7.56 (m, 4H), 7.68 (s, 1H), 9.37 (s, 1H); IR (solid) 3350, 3050, 1590, 1520, 1460, and 1230 cm−1; [ESI(+)], m/z 314 (M+H)+; Anal. Calcd. for C22H19NO: C, 84.31; H, 6.11; N, 4.47; Found: C, 84.21; H, 6.37; N, 4.38.

Provenance & Evidence