Water → Quinoline

Participants

Reaction Steps

0.2 g (6.38×10−4 mol) of 1,1-dibromo-2-(2-quinolyl)ethene obtained from 2-formylquinoline, carbon tetrabromide (CBr4) and triphenylphosphine (PPh3) (Ramirez et al., J. Am. Chem. Soc., 1962, 84: 1745) and 11.28 mg (3.19×10−5 mol, 5 mol %) of iron triacetylacetonate (Fe(acac)3) are dissolved in 3 ml of anhydrous THF and 3 ml of anhydrous N-methylpyrrolidone (NMP) at −10° C., in a dry round-bottomed flask equipped with a magnetic stirrer and a nitrogen inlet. 0.39 ml (7.02×10−4 mol) of a 1.8M solution of isopropyl magnesium bromide in THF is added dropwise to the solution. After stirring for 30 minutes, the reaction is hydrolyzed with 10 ml of water and the solution is brought back to ambient temperature. Next, the two phases are separated and the aqueous phase is extracted with diethyl ether (3×30 ml).

Provenance & Evidence