Hydrochloric Acid → 1-[3-(2-Chloro-1-chloromethyl-ethoxy)-2-nitro-phenylmethanesulfonyl]-naphthalene

HRID 33107Notes

Reaction equation

[Cl:1][CH2:2][CH:3]([CH2:14][Cl:15])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12].Cl[CH2:17][S:18]([C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19].CC(C)([O-])C.[K+].Cl>C1COCC1>[Cl:1][CH2:2][CH:3]([CH2:14][Cl:15])[O:4][C:5]1[C:6]([N+:11]([O-:13])=[O:12])=[C:7]([CH2:17][S:18]([C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23][CH:22]=2)(=[O:19])=[O:20])[CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: -40 °C

Procedure

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.

Workup

customto rise to −40° C
extractionextracted with EtOAc
dry with materialdried over Na2SO4
concentrationconcentrated under vacuum
customThe resultant solid residue was recrystallized from CH2Cl2/hexane

Sources & evidence

ORD record: ord-729665a8979c497190491e7ff9009077
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429582B2

Reaction notes

Loading…