Sodium Iodide → 6-Bromo-4-(methoxymethyl)-2H-1,4-benzoxazin-3(4H)-one

Participants

Reaction Conditions

Reaction Steps

A suspension of 6-bromo-2H-1,4-benzoxazin-3(4H)-one (13 g, 57 mmol) in 1,2-dichloroethane (350 ml) was cooled in an ice bath to which N,N-diisopropylethylamine (119 ml), sodium iodide (10.25 g, 68.4 mmol) and chloromethylmethyl ether (43.3 ml, 570 mmol) were added, and the mixture was stirred at 70° C. for 3 hours. After cooling, the reaction mixture was diluted with dichloromethane, washed with cold water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to yield 13.6 g (88%) of the title compound in the form of a light brown solid.

Provenance & Evidence