1,4-Dibromobenzene → Benzene, 1-bromo-4-(2-propenyl)-

Temperature

-10 °C

Cyclopentyl methyl ether (CPME) (90 ml) was added to 1,4-dibromobenzene (1) (15 g, 15.9 mmol) under a nitrogen atmosphere, the mixture was cooled to around −10° C. with brine ice, a solution of 2 M isopropylmagnesium chloride in tetrahydrofuran (THF) (iPrMgCl solution) (0.35 equivalent amount, 11.2 ml) and a solution of 1.67 M n-butyllithium in hexane (nBuLi solution) (0.7 equivalent amount, 26.8 ml) were respectively added dropwise. The mixture was stirred at around −10° C. for 2 hours, allyl bromide (1.1 equivalent amount, 6.8 ml) was then added, and the mixture was stirred at room temperature for 14 hours. Diethyl ether was added to the reaction mixture, and the mixture was neutralized with a saturated aqueous solution of ammonium chloride. The aqueous layer was extracted with diethyl ether, and the combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under a reduced pressure to give a crude product of 1-allyl-4-bromobenzene (2) (yield amount: 13.0 g, tentative yield: 103%), as shown in the following chemical reaction formula.

1. stirringthe mixture was stirred at room temperature for 14 hours
2. extractionThe aqueous layer was extracted with diethyl ether
3. washthe combined organic layer was washed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under a reduced pressure

ORD record

ord-08fcb286ee044768b09a118e316cc6ae

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409929B2