Water → 1-Bromo-4-(3-bromopropoxy)benzene

To a suspension of 4-bromophenol (2.00 g, 11.56 mmol) and potassium carbonate (4.79 g, 34.68 mmol) in DMF (12 mL) was added 1,3-dibromopropane (7.00 g, 37.3 mmol). The mixture was stirred at room temperature overnight. 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 (0-5% ethyl acetate/petroleum ether to afford the title compound (2.35 g, 69%) as a colorless oil. 1H NMR (400 MHz, CDCl3) ppm 7.39 (d, 2 H), 6.80 (d, 2 H), 4.16-4.01 (m, 2 H), 3.55-3.53 (m, 2 H), 2.41-2.26 (m, 2 H).

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

ORD record

ord-4254b86d245f4fd2a8e245e99fe781f0

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394285B2