Iodine → HCID 118193084, compound

Participants

Reaction Steps

Under nitrogen atmosphere, n-butyl lithium (1.63 M (solvent: hexane), 0.46 ml, 0.75 mmol) was dripped into a THF solution (5 ml) of 3-(phenylsulfenyl)naphtho[2,3-b]thiophene (146 mg, 0.5 mmol) at 0° C. After the mixture was stirred for 1 hour at room temperature, iodine (190 mg, 0.75 mmol) was added thereto at 0° C. and the mixture was stirred for further 6 hours at room temperature. Subsequently an aqueous solution of Na2S2O5 was added thereto, and the mixture was extracted with CH2Cl2 (50 ml×3) and washed with saline (15 ml×3). The extract liquid was dried with magnesium sulfate, and concentrated. Purification was implemented by column chromatography (silica gel, CHCl3, Rf: 0.9), so that 3-(phenylsulfenyl)-2-iodonaphtho[2,3-b]thiophene was produced as an orange solid (138 mg, 0.3 mmol, yield: 66%).

Provenance & Evidence