Bromine → HCID 19858046, compound

Participants

Reaction Steps

A mixture of 1,2-dihydro-1,1,8-trimethyl-2-oxonaphtho[2,1-b]furan-7-carbonitrile (0.25 g), silver trifluoromethanesulphonate (0.34 g) and dichloromethane (10 ml) was stirred in the dark, while a solution of bromine (0.19 g) in dichloromethane (2 ml) was added over 10 minutes. The mixture was stirred a further 0.5 h, then treated with aqueous sodium hydrogen carbonate solution, and the resulting mixture was filtered through a pad of diatomaceous earth ("Celite" -trade mark). The organic phase was separated, dried and evaporated to dryness under reduced pressure. The residue was purified by flash chromatography, using chloroform:pentane, 1:1 v/v, as eluant, to give 9-bromo-1,2-dihydro-1,1,8-trimethyl-2-oxonaphtho[2,1-b]furan-7-carbonitrile, m.p. 235°-237° after recrystallisation from a mixture of ethyl acetate and petroleum ether (b.p. 60°-80°), which was brominated by the process described in the last part of Example 4.

Provenance & Evidence