Benzoyl Peroxide → 2-(Benzenesulfonyl)-3-[4-(bromomethyl)phenyl]prop-2-enenitrile

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Reaction Steps

56.8 g (0.2 mole) of 1-p-tolyl-2-cyano-2-phenylsulfonylethylene were dissolved in 1.000 ml of anhydrous carbon tetrachloride at 40° to 50° C. After addition of 35.6 g (0.2 mole) of N-bromosuccinimide and 1.2 g of dibenzoylperoxide, the whole was heated to the boil under reflux. After 5 hours, the mixture was filtered by still hot; as residue 17.2 g (about 86%) of succinimide melting at 125° C remained behind. The filtrate was evaporated on a rotary steamer and under the vacuum produced by a water jet and the residue was recrystallized from 400 ml of ethanol. 47.4 g (65 of the theory) of weakly yellow crystal melting at 120° to 122° C were isolated. Characteristical NMR-signal in CDCl3 /TMS: --CH2Br at δ = 4.6 ppm. ##STR15##

Provenance & Evidence