Hydrochloric Acid → 1-[3-(2-Chloro-ethoxy)-5-methoxy-2-nitro-phenylmethanesulfonyl]-naphthalene

HRID 2240063Notes

Reaction equation

HRID 2240063 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14].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][CH2:3][O:4][C:5]1[C:6]([N+:13]([O-:15])=[O:14])=[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]=[C:9]([O:11][CH3:12])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 117366081-((Chloromethyl)sulfonyl)naphthaleneHCID 23665647Potassium tert-butoxideHCID 686798742-(2-Chloroethoxy)-4-methoxy-1-nitrobenzene

Product 1

HCID 686804311-[3-(2-Chloro-ethoxy)-5-methoxy-2-nitro-phenylmethanesulfonyl]-naphthaleneYield 76.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(2-chloro-ethoxy)-4-methoxy-1-nitrobenzene (1.4 g, 6 mmoles) and 1-chloromethane-sulfonyl-naphthalene (1.4 g, 6 mmoles) was stirred in THF (50 mL) at −78° C., in a round bottom flask under nitrogen. A solution of 1M potassium t-butoxide was added dropwise (18 mL, 18 mmoles) over a half an hour period. Temperature was allowed to rise to −40° C., and the reaction mixture was stirred at this temperature for 4 hours. The reaction mixture was poured into cold 2N HCl, extracted with EtOAc, dried over Na2SO4, and concentrated under vacuum. Compound was recrystallized from CH2Cl2/hexane to afford the title compound as an off-white solid (2 g, 4.6 mmoles).

Workup

  1. customto rise to −40° C.
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customCompound was recrystallized from CH2Cl2/hexane

Sources & evidence

ORD record
ord-b60aaf61883c4f1d8a6c08145678cd78
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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