Boron tribromide → HCID 68813887, compound

Participants

Reaction Steps

The desired product was prepared using a procedure similar to step 4 of example 3. Thus, 4-(4-methoxy-phenyl)-1,3-dimethyl-2-phenyl-1H-indole (1.227 g, 3.747 mmol) was reacted with BBr3 (4.5 ml of a 1M solution in CH2Cl2) to give the product (0.751 g, 2.396 mmol, 64%) as a white solid, mp 132-134° C. 1H NMR (DMSO-d6) δ 1.71 (s, 3H), 3.57 (s, 3H), 6.78-6.83 (m, 3H), 7.15-7.19 (m, 3H), 7.40-7.46 (m, 4H), 7.52 (t, J=7.2 Hz, 2H), 9.39 (s, 1H); IR (solid) 3480, 3430, 2920, 1605, 1520, 1480, 1450, 1310, 1270, and 1180 cm−1; [ESI(+)], m/z 314 (M+H)+; Anal. Calcd. for C22H19NO: C, 84.31; H, 6.11; N, 4.47; Found: C, 84.17; H, 6.10; N, 4.42.

Provenance & Evidence