Reaktion #61385

Reaktionsgleichung

HCl

1-(2-chloro-1-chloromethyl-ethoxy)-2-nitro-benzene

1-chloromethane-sulfonyl-naphthalene

potassium t-butoxide

→

title compound

Ausbeute 66.3%

1-[3-(2-Chloro-1-chloromethyl-ethoxy)-2-nitro-phenylmethane-sulfonyl]-naphthalene

Ausbeute 66.3%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto rise to −40° C
2. 2
   Extraktionextracted with EtOAc
3. 3
   Trocknendried over Na2SO4
4. 4
   Einengenconcentrated under vacuum
5. 5
   SonstigeThe resultant solid residue was recrystallized from CH2Cl2/hexane

Vorschrift

A mixture of 1-(2-chloro-1-chloromethyl-ethoxy)-2-nitro-benzene (2) (2.0 g, 8 mmoles) and 1-chloromethane-sulfonyl-naphthalene (2.88 g, 12 mmoles) in THF at −78° C., under nitrogen, was treated dropwise over a 30 minute period with a solution of 1M potassium t-butoxide (18 ml, 18 mmoles). The reaction temperature was allowed to rise to −40° C. The reaction mixture was 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 solid residue was recrystallized from CH2Cl2/hexane to afford the title compound as an off-white solid (2.4 g, 5.3 mmoles), identified by HNMR analysis.

Quelle