p-Fluoronitrobenzene → 1-(5-Fluoro-2-nitrobenzylsulfonyl)naphthalene

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 4-fluoro-nitrobenzene (1 equiv.) and chloromethyl-1-naphthylsulfone (1 equiv.) in dry THF under nitrogen at −78° C., was treated with 1.0 M KOt-Bu (2.2 equiv., 1.0 M in THF), warmed to −20° C. over 1 h period, quenched with acetic acid and treated sequentially with water, saturated aqueous NaHCO3 and extracted with ether. The combined extracts were washed with water and brine, dried over MgSO4 and concentrated in vacuo. The resulting residue was chromatographed (Silica gel, 1:1 and 1:0 ethyl acetate:hexanes as eluent) to give 1-(5-fluoro-2-nitrobenzyl-sulfonyl)naphthalene.

Provenance & Evidence