Iodine → HCID 19384259, compound

Participants

Reaction Steps

A mixture of the product of step 1 (5.27 g, 14.7 mmol), Methanol (50 cm3), zinc powder (9.66 g, 147 mmol), zinc iodide (catalytic), and iodine (catalytic) was refluxed for 18 hours. The reaction mixture was filtered and the filtrate partitioned between diethyl ether and 1.4M hydrochloric acid. The organic phase was washed with water, dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure to give a brown oil. Chromatography on silica gel using 8:2 hexane:ethylacetate as eluent afforded the product as a white solid (2.13g). 1H NMR (CDCl3): δ7.45(1H,d); 6.95(1H,d); 6.8(1H,dd); 6.1(1H,s); 4.2-4.4(1H,m); 3.3(2H,t); 2.5(2H,m). M+ =257. m.p. 73.6°-75.4° C.

Provenance & Evidence