Experimental and Theoretical Investigations of the Bromination of Phenols with β and γ Aliphatic Substituents, including Rings.

Bromination reactions of substituted and ring fused phenols were studied by both experiment (t-BuNH-Br) and computation (density functional theory). The outcomes support each other, indicating a clear and predictable regioselective preference among 3,4-bis-alkylated and 3,4-ring-fused phenols.