Hydrochloric Acid → HCID 68679905, compound

HRID 2240053Notes

Reaction equation

HRID 2240053 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12].[C:14]1([S:20](CCl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:25]C(C)([O-])C.[K+].Cl>C1COCC1>[C:14]1([S:20]([C:7]2[CH:8]=[CH:9][C:10]([CH3:25])=[C:5]([O:4][CH2:3][CH2:2][Cl:1])[C:6]=2[N+:11]([O-:13])=[O:12])(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81625((Chloromethyl)sulphonyl)benzeneHCID 43624871-(2-chloroethoxy)-2-nitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 68679905HCID 68679905, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(2-chloro-ethoxy)-2-nitrobenzene (1.2 g, 6 mmoles) and chloromethyl phenyl sulfone (2.16 g, 9 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 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 (1.5 g, 4.2 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-eb153d6d4e964bda9f0254137de40084
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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