Hydrochloric Acid → 1-[5-(4-Chloro-butoxy)-2-nitro-phenylmethanesulfonyl]-naphthalene

HRID 2240042Notes

Reaction equation

HRID 2240042 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1.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][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]([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]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 117366081-((Chloromethyl)sulfonyl)naphthaleneHCID 145719461-(4-Chloro-butoxy)-4-nitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 686789021-[5-(4-Chloro-butoxy)-2-nitro-phenylmethanesulfonyl]-naphthaleneYield 80.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(4-chloro-butoxy)-4-nitrobenzene (1.28 g, 5.6 mmoles) and 1-chloromethane-sulfonyl-naphthalene (1.6 g, 6.72 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 (16.8 ml, 16.8 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 5 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 (1.94 g, 4.5 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-1e508f5b05894e018e3efcf70f03084a
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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