Acetic Acid → 2-Nitrobenzyl phenyl sulfone

HRID 890009

Reaktionsgleichung

Reaktionsgleichung von HRID 890009
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[CH2:11][S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13].CC([O-])(C)C.[K+].C1COCC1.C(O)(=O)C>C1COCC1.O>[C:15]1([S:12]([CH2:11][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])(=[O:14])=[O:13])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 7416NitrobenzeneHCID 81625((Chloromethyl)sulphonyl)benzeneHCID 66863523KOtBu THF

Produkt 1

HCID 3638902-Nitrobenzyl phenyl sulfoneAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

A solution of nitrobenzene (3.08 g, 25.0 mmol) and chloromethylphenylsulfone (4.76 g, 25.0 mmol) in dry THF is cooled to −50° C. and treated with 1.0M KOtBu/THF (55.0 mL, 55.0 mmol). The reaction is allowed to warm to −30° C. over 1 h, treated with glacial acetic acid (3.6 mL), warmed to 20° C., treated with water and extracted with CH2Cl2. The combined extracts are dried over MgSO4 and concentrated in vacuo. Chromatography (1:1 ethyl acetate:hexanes) of the resultant residue give the title product as a white solid, 5.62 g, (81% yield), mp 106–108° C., identified by mass spectral and HNMR analyses.

Aufarbeitung

  1. temperaturewarmed to 20° C.
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined extracts are dried over MgSO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-09a60ac6dee44830aacafc552fe666b2
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06995176B2

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