Hydrogen Peroxide → HCID 23216865, compound

Participants

Reaction Steps

[2-(Benzyloxy)-5-bromophenyl]methanol (140.3 g) was dissolved in 700 ml of toluene, 160 g of diphenyl phosphorazide and 85 g of diazabicyclodecene were successively added to the solution, and the mixture was stirred overnight at room temperature. 1 L of ethyl acetate was added thereto, and the reaction mixture was successively washed with water and brine, dried over anhydrous magnesium sulfate, and the solvent was removed to give 157 g of 1-[2-(benzyloxy)-5-bromobenzyl]-1,2-triazadien-2-ium. 47.23 g of the product was dissolved in 500 ml of tetrahydrofuran and 20 ml of water, 42 g of triphenyl phosphine was added thereto, and the mixture was stirred overnight. 28 g of t-butyl dicarbonate was added thereto and stirred at room temperature for 1 hour, and 3 ml of 30% aqueous hydrogen peroxide was added thereto. The solvent was concentrated and the residue was suspended in diethyl ether and filtered. The filtrate was evaporated, and the residue was purified by silica gel column, to give 47.645 g of the title compound in the 15:1→10:1 hexane-ethyl acetate fraction.

Provenance & Evidence