Water → HCID 19919984, compound

Participants

Reaction Steps

2 g of 60 wt % sodium hydride were added to 45 ml of tetrahydrofuran under stirring at room temperature, followed by drop-wise addition thereto of a solution of 9.9 g of 3-chloro-2-mercapto-5-trifluoromethylpyridine in 40 ml of tetrahydrofuran. After completion of the drop-wise addition, the reaction mixture was heated under reflux for 30 minutes, and cooled to room temperature, followed by drop-wise addition thereto of a solution of 10 g of 2-nitrobenzyl bromide in 60 ml of tetrahydrofuran. After completion of the drop-wise addition, stirring was continued at room temperature for 15 hours. The reaction mixture was poured into water, subjected to extraction with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent:methylene chloride:hexane=4:1) to obtain 12 g of 2-(3-chloro-5-trifluoromethyl-2-pyridylthiomethyl)nitrobenzene.

Provenance & Evidence