Dimethylformamide → Benzene, [[2-(bromomethyl)-2-propenyl]sulfonyl]-

Temperature

100 °C

A solution of crude (2-chloromethyl-prop-2-ene-1-sulfonyl)-benzene (186 g, assumed 0.80 mmol) in a mixture of dibromomethane (400 ml) and of dimethylformamide (800 ml) was stirred at room temperature during the addition of sodium bromide (82 g, 0.80 mmol). The resulting suspension was stirred at 100° C. for 16 hours, then cooled to room temperature and concentrated in vacuo. The crude material was dissolved in of ethyl acetate (750 ml) and the resulting solution was washed with water (750 ml) and brine (750 ml), dried (anhydrous magnesium sulfate) and concentrated in vacuo. The crude product was recrystallised from isopropyl ether to give (2-bromomethyl-prop-2-ene-1-sulfonyl)-benzene (82 g, 37%). Mass spectrum 276 [M+H]+.

1. temperaturecooled to room temperature
2. concentrationconcentrated in vacuo
3. dissolutionThe crude material was dissolved in of ethyl acetate (750 ml)
4. washthe resulting solution was washed with water (750 ml) and brine (750 ml)
5. dry with materialdried (anhydrous magnesium sulfate)
6. concentrationconcentrated in vacuo
7. customThe crude product was recrystallised from isopropyl ether

ORD record

ord-a1f18c946221489caa1d8f857e08e7dd

Source dataset

uspto-grants-2003_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06632826B1