Iodine → HCID 19081622, compound

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Reaction Steps

1.2 g of 1,7-bis-methoxymethoxy-naphthalene are dissolved in 9 ml of THF and cooled to -78°. 3.13 ml of a 1.6M n-butyl-lithium solution in hexane are added dropwise thereto and the mixture is stirred at room temperature overnight. Subsequently, it is again cooled to -78° and a solution of 1.25 g of iodine in 3.4 ml of THF is added dropwise. The mixture is warmed to room temperature and 10 ml of saturated ammonium chloride solution are added. The organic solvents are evaporated on a rotary evaporator and the residue is extracted three times with ether. After drying and evaporation the residue is chromatographed on silica gel with ethylene chloride. 0.72 g of 8-iodo-1,7-bis-methoxy-naphthalene is thus isolated. Yield: 40%. Mass spectrum: peaks inter alia at 374 (M+, 87%), 171 (40%), 45 (100%).

Provenance & Evidence