Boron tribromide → 4-(9-Benzyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenol

Participants

Reaction Steps

The desired product was prepared using a procedure similar to step 4 of example 3. Thus, 9-benzyl-6-(4-methoxy-phenyl)-2,3,4,9-tetrahydro-1H-carbazole (1.930 g, 5.252 mmol) was reacted with BBr3 (6.3 ml of a 1M solution in CH2Cl2) to give the product (0.840 g, 2.377 mmol, 45%) as a pale-green foam. 1H NMR (DMSO-d6) δ 1.78-1.85 (m, 4H), 2.63-2.70 (m, 4H), 5.32 (s, 2H), 6.81 (d, J=8.4 Hz, 2H), 7.03 (d, J=7.5 Hz, 2H), 7.19-7.23 (m, 2H), 7.28 (t, J=7.6 Hz, 2H), 7.36 (d, J=8.6 Hz, 1H), 7.44 (d, J=8.6 Hz, 2H), 7.53 (s, 1H), 9.32 (s, 1H); [ESI(+)], m/z 354 (M+H)+.

Provenance & Evidence