Water → 1-Bromo-3-butylbenzene

Temperature

0 °C

Under nitrogen stream, to a solution of 1-bromo-3-bromomethylbenzene (25 g) in tetrahydrofuran (200 ml) were sequentially added dropwise n-propylmagnesium bromide (60 ml, 2M solution in tetrahydrofuran) and lithium tetrachlorocuprate (5 ml, 0.1M solution in tetrahydrofuran) at −78° C. Then, this reaction mixture was stirred at 0° C. for 2 hours. Under ice-cooling, to this reaction mixture were sequentially added a saturated aqueous solution of ammonium chloride (100 ml) and water (100 ml), and the mixture was extracted with ethyl acetate (200 ml). The resulting aqueous layer was again extracted with ethyl acetate (100 ml), the combined organic layer was washed with a saturated aqueous solution of sodium chloride (100 ml), and dried over anhydrous sodium sulfate. This organic layer was concentrated under reduced pressure, the resulting residue was purified by silica gel chromatography (eluent: n-hexane/ethyl acetate=1/0 to 100/1) to give the titled compound (8.5 g).

1. temperatureUnder ice-cooling, to this reaction mixture
2. extractionthe mixture was extracted with ethyl acetate (200 ml)
3. extractionThe resulting aqueous layer was again extracted with ethyl acetate (100 ml)
4. washthe combined organic layer was washed with a saturated aqueous solution of sodium chloride (100 ml)
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationThis organic layer was concentrated under reduced pressure
7. customthe resulting residue was purified by silica gel chromatography (eluent: n-hexane/ethyl acetate=1/0 to 100/1)

ORD record

ord-d13bbf0564d04658a888a63850f10bbb

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846746B2