1,2-Dibromoethane → 1-(2-Bromoethoxy)-3,5-dichlorobenzene

To a solution of NaOH (2.45 g, 61.3 mmol) in water (20 mL) was added 3,5-dichlorophenol (5 g, 30.7 mmol). The solution was heated at reflux for 1 h and was cooled to room temperature. 1,2-Dibromoethane (11.52 g, 61.3 mmol) was added and the reaction was heated at reflux for 24 h. The cooled solution was diluted with EtOAc and the organic solution was washed sequentially with HCl (1N, 1×), water (1×), and brine (1×). The organic solution was dried (MgSO4), filtered, and concentrated. Purification by flash chromatography (hexanes to 5% EtOAc in hexanes) provided the title compound (3.79 g). 1H NMR (400 MHz, CDCl3) δ 6.98 (m, 1H), 6.82 (m, 2H), 4.25 (t, 2H), 3.61 (t, 2H).

1. temperatureThe solution was heated
2. temperatureat reflux for 1 h
3. temperaturethe reaction was heated
4. temperatureat reflux for 24 h
5. washthe organic solution was washed sequentially with HCl (1N, 1×), water (1×), and brine (1×)
6. dry with materialThe organic solution was dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customPurification by flash chromatography (hexanes to 5% EtOAc in hexanes)

ORD record

ord-f4f0a930b81f4a14ae476141e5591c37

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06498172B1