2-Bromophenol → 1-Bromo-2-(2-methoxyethoxy)benzene

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromophenol (500.0 mg, 2.89 mmol) in DMF (5 mL) was added cesium carbonate (2.82 g, 8.67 mmol). To this mixture was added 1-chloro-2-methoxyethane (0.26 mL, 2.89 mmol, Aldrich) and the mixture was heated at 90° C. for 4 h. After completion, the reaction mixture was diluted with water (3 mL) and extracted with ethyl acetate (2×10 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to get 1-bromo-2-(2-methoxyethoxyl)benzene (400 mg, 60.2%) as clear liquid that was used as such for next step without any purification. 1H NMR (400 MHz, DMSO) δ 7.57 (dd, J=7.9, 1.5 Hz, 1H), 7.39-7.24 (m, 1H), 7.13-7.05 (m, 1H), 6.89 (td, J=7.7, 1.2 Hz, 1H), 4.17 (t, J=4.6 Hz, 2H), 3.69 (t, J=4.6 Hz, 2H), 3.33 (s, 3H). MS (ESI, positive ion) m/z: 231.08 (M+1).

Provenance & Evidence