Hydrochloric Acid → 1-[3-(2-Chloroethoxy)-5-fluoro-2-nitrophenylmethanesulfonyl]-naphthalene

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(2-chloroethoxy)-4-fluoro-1-nitro-benzene (1.3 g, 6 mmoles) and 1-chloromethane-sulfonyl-naphthalene (2.16 g, 9 mmoles) in THF, under nitrogen, was stirred at −78° C., treated dropwise with a solution of 1M potassium t-butoxide (18 ml, 18 mmoles) over a 30 min. period, allowed to warm to −40° C., stirred at −40° C. for 5 hours, poured into cold 2N HCl and extracted with EtOAc. The extracts were combined, dried over Na2SO4, and concentrated under vacuum. The resultant residue was recrystallized from CH2Cl2/hexane to afford the title compound as an off-white solid (2.25 g, 5.3 mmoles), identified by HNMR and mass spectral analyses.

Provenance & Evidence