Water → 1-Bromo-4-(propan-2-yloxy)benzene

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromophenol (16-2, 7.02 g, 39.4 mmol) and potassium carbonate (12.6 g, 90.9 mmol) in DMSO (20.0 mL) was added with 2-iodopropane (16-1, 5.2 mL, 49.0 mmol). The mixture was heated at 60° C. overnight. The solution was cooled to room temperature and added with water (200 mL). The reaction was extracted with EtOAc, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (EtOAc:hexanes=1:100 as eluant) to give 1-bromo-4-isopropoxybenzene (6.66 g) as colorless oil in 79% yield: 1H NMR (CDCl3) δ 7.34 (m, 2 H), 6.77 (dd, J=8.9, 3.1 Hz, 2 H), 4.49 (m, 1 H), 1.33 (s, 3 H), 1.31 (m, 3 H).

Provenance & Evidence