1-Iodo-4-nitrobenzene → 1,2-Dichloro-3-(4-nitrobenzyl)benzene

Participants

Reaction Steps

Under an argon stream, bis(dibenzylidenacetone)palladium(0) (3.2 g, 5.6 mmol) and tri(2-furyl)phosphine (2.6 g, 11.2 mmol) were dissolved in THF (310 ml), the reaction mixture of 2,3-dichlorobenzylzinc chloride (421.7 mmol) in THF obtained in Reference Example 1 was added dropwise under ice-cooling through a cannula, and then a solution of 4-iodonitrobenzene (70.0 g, 281 mmol) in THF (700 ml) was added dropwise, after which the mixture was stirred at room temperature for 2 hr, saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was filtered through celite. The filtrate was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the precipitated solid was collected by filtration on the way. The filtrate was again concentrated under reduced pressure, and the precipitated solid was collected by filtration on the way. The collected solids were combined washed with n-hexane and vacuum dried to give the object product (60.2 g, yield 76%) as a pale-brown solid.

Provenance & Evidence