Potassium Iodide → 8-cyanomethyl-2-(3-fluorophenyl)-4H-benzopyran-4-one

Participants

Reaction Steps

A suspension of 11.2 g of the above prepared 8-bromomethyl-2-(3-fluorophenyl)-4H-benzopyran-4-one, 3.2 g of potassium cyanide, 5.7 g of potassium iodide and 1.3 g of aliquot 336 (tricaprylylmethylammonium chloride) in 45 ml of water and 485 ml of toluene was stirred for 25.5 hours at 73° C., cooled, diluted with water and extracted with methylene chloride. The solvents in the organic layer were concentrated in vacuo and the resulting residue chromatographed over silica gel with 3-5% acetone in a 1:1 mixture of methylene chloride and hexane to give 4.6 g of 8-cyanomethyl-2-(3-fluorophenyl)-4H-benzopyran-4-one. IR 1643 cm-1 ; NMR (CDCl3): δ 4.06 (2, 1H), 6.8 (s, 1H), 7.0-7.85 (m, 6H), 8.2 (m, 1H).

Provenance & Evidence