2-Bromophenol → 1-bromo-2-(2-bromoethoxy)benzene

Temperature

80 °C

A suspension of 2-bromophenol (3.50 g, 20.23 mmol), 1,2-dibromoethane (19.00 g, 101 mmol), and potassium carbonate (7.06 g, 2.92 mmol) in acetonitrile (50 mL) was heated to 80° C. After heating overnight, the reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with water and saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered and the filtrate was concentrated in vacuo to afford the title compound as a clear oil. Yield: 6.36 g, 100%. 1H NMR (400 MHz, CDCl3) δ 3.69 (dd, J=6.6, 6.4 Hz, 2H), 4.35 (dd, J=6.7, 6.4 Hz, 2H), 6.87-6.94 (m, 2H), 7.25-7.30 (m, 1H), 7.56 (dd, J=7.9, 1.6 Hz, 1H).

1. temperatureAfter heating overnight
2. temperaturethe reaction mixture was cooled to room temperature
3. washwashed with water and saturated aqueous sodium chloride solution
4. dry with materialThe organic layer was dried over magnesium sulfate
5. filtrationfiltered
6. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-1e2ee62ebde04d58ab5b06f5a8e34e97

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067934B2