2-Bromoethanol → 2-(3-BroMo-phenoxy)-ethanol

To a solution of 3-bromophenol (36.38 g, 210.3 mmol) in acetone (175 ml) was added K2CO3 (0.033 g, 237 mmol) and 2-bromoethanol (20 ml, 283.3 mmol). The reaction mixture was heated at reflux under argon for 4 days. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in diethyl ether (150 ml) and the solution was washed successively with water, 10% aqueous NaOH, 5% aqueous NaOH, water, and brine. The solution was dried over MgSO4 and concentrated under reduced pressure to give 2-(3-bromophenoxyl)ethanol (106) as a light brown oil. Yield (21.07 g, 46%): 1H NMR (400 MHz, CDCl3) δ 7.14 (t, J=7.8 Hz, 1H), 7.07-7.12 (m, 2H), 6.85 (ddd, J=7.8, 2.4, 1.3 Hz, 1H), 4.05-4.07 (m, 2H), 3.93-3.97 (m, 2H), 2.11 (t, J=12.3 Hz. 1H).

1. temperatureThe reaction mixture was heated
2. temperatureat reflux under argon for 4 days
3. filtrationthe mixture was filtered
4. concentrationthe filtrate was concentrated under reduced pressure
5. dissolutionThe residue was dissolved in diethyl ether (150 ml)
6. washthe solution was washed successively with water, 10% aqueous NaOH, 5% aqueous NaOH, water, and brine
7. dry with materialThe solution was dried over MgSO4
8. concentrationconcentrated under reduced pressure

ORD record

ord-ac8d963bc27b4539a9f6d7af913ca0c9

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09314467B2