4-Bromophenol → 2-Bromoethyl p-bromophenyl ether

To a suspension of 4-bromophenol (2.00 g, 11.6 mmol) in water (20 mL) was added 1,2-dibromoethane (5.40 g, 28.8 mmol) and sodium hydroxide (0.700 g, 17.5 mmol). Then, the mixture was heated at reflux for 12 hours. Water was added, and the mixture was extracted with ethyl acetate (4×30 mL). The combined organic layers were washed with brine (3×20 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the crude product. The crude product was purified by flash chromatography (0-10% ethyl acetate/petroleum ether) to afford the title compound (1.8 g, 56%) as a colorless oil.

1. temperatureThen, the mixture was heated
2. temperatureat reflux for 12 hours
3. extractionthe mixture was extracted with ethyl acetate (4×30 mL)
4. washThe combined organic layers were washed with brine (3×20 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto give the crude product
9. customThe crude product was purified by flash chromatography (0-10% ethyl acetate/petroleum ether)

ORD record

ord-76972e3d4d0f418488263a62fece5f48

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889730B2