Acetic Acid → 2-Nitrobenzyl phenyl sulfone

Participants

Reaction Conditions

Reaction Steps

A solution of nitrobenzene (3.08 g, 25.0 mmol) and chloromethylphenylsulfone (4.76 g, 25.0 mmol) in dry THF is cooled to −50° C. and treated with 1.0M KOtBu/THF (55.0 mL, 55.0 mmol). The reaction is allowed to warm to −30° C. over 1 h, treated with glacial acetic acid (3.6 mL), warmed to 20° C., treated with water and extracted with CH2Cl2. The combined extracts are dried over MgSO4 and concentrated in vacuo. Chromatography (1:1 ethyl acetate:hexanes) of the resultant residue give the title product as a white solid, 5.62 g, (81% yield), mp 106-108° C., identified by mass spectral and HNMR analyses.

Provenance & Evidence