Iodine → HCID 88552651, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, n-butyllithium (1.65 M, 14.1 mL, 23.26 mmol) was slowly added dropwise, at −60° C. or lower, to a THF (50 mL) solution of compound (87) (6.44 g, 19.38 mmol). The reaction mixture was agitated at −60° C. or lower for 1 hour, and then a THF (30 mL) solution of iodine (5.9 g, 23.26 mmol) was added dropwise thereto. The reaction mixture was returned to room temperature, and then quenched with a saturated aqueous solution of ammonium chloride, and extracted with 50 mL of toluene three times. Combined organic layers were washed with a sodium thiosulfate aqueous solution, a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, and then dried over magnesium sulfate, and a solvent was distilled off by an evaporator. The residue was purified by silica gel column chromatography, and thus 2-ethoxy-1,8,9,9,10,10-hexafluoro-7-iodo-9,10-dihydrophenanthrene (88) (6.7 g, yield 74.5%) was obtained.

Provenance & Evidence