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

HRID 2219009Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13].Cl[CH2:16][S:17]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)(=[O:19])=[O:18].CC(C)([O-])C.[K+].Cl>C1COCC1>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH2:16][S:17]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)(=[O:18])=[O:19])[CH:8]=[C:9]([F:11])[CH:10]=1

Participants

Conditions

Temperature: -78 °C

Procedure

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.

Workup

temperatureto warm to −40° C.
stirringstirred at −40° C. for 5 hours
extractionextracted with EtOAc
dry with materialdried over Na2SO4
concentrationconcentrated under vacuum
customThe resultant residue was recrystallized from CH2Cl2/hexane

Sources & evidence

ORD record: ord-f6876681029143ee89f82713571ab346
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414051B2

Reaction notes

Loading…