1-Ethenyl-4-nitrobenzene → HCID 178502925, compound

Participants

Reaction Conditions

Reaction Steps

0.665 g of crystalline hypophosphorous acid was treated under nitrogen with 1.73 g of trimethyl orthoformate and the mixture was stirred at 20° C. for 2 hours. The resulting solution of crude methyl hypophosphite was added dropwise at 0° C. to a solution of 1 g of 4-nitrostyrene and 0.43 g of diisopropylethylamine in 5 ml of methanol. After 65 hours at 20° C. the same amount of methyl hypophosphite was again added and the mixture was stirred at 20° C. for a further 24 hours. The mixture was diluted with 30 ml of water and the pH was adjusted to 7 with aqueous sodium bicarbonate solution. After extraction with dichloromethane and chromatography on silica gel using 10% methanol in ethyl acetate for the elution there was obtained 0.5 g of 1-[2-(methoxyphosphinyl)ethyl]-4-nitrobenzene in the form of a yellow liquid.

Provenance & Evidence