Hydrochloric Acid → 7-tert-butyl-2,3-dihydro-3,3-dimethylbenzothiophene

HRID 1488577Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1488577
[CH:1]([S:5][C:6]1[C:11]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1Br)=[C:2]([CH3:4])[CH3:3].[PH2](O)=O.C(N(CC)CC)C.Cl>O1CCOCC1.[Cl-].[Na+].O>[CH3:3][C:2]1([CH3:4])[CH2:1][S:5][C:6]2[C:11]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:10][CH:9]=[CH:8][C:7]1=2

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 4124402Phosphinic AcidHCID 22905880HCID 22905880, Verbindung

Produkt 1

HCID 107041827-tert-butyl-2,3-dihydro-3,3-dimethylbenzothiophene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 312751,4-DioxaneLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
24 °C

Versuchsvorschrift

A solution of 2-bromo-6-tert-butylphenyl isobutenyl thioether (600 mg, 2.07 mmol), 90% hypophosphorous acid (4.4 g, 60 mmol), and triethylamine (8.4 mL, 60 mmol) in dioxane (30 mL) is deoxygenated by bubbling with N2 for 20 min. The solution is then heated under N2 to reflux, and a solution of azo-bis-isobutyrylnitrile (205 mg, 1.04 mmol) in deoxygenated dioxane (2 mL) is added in 0.2-mL portions over 3 h. The reaction is allowed to cool to 24° C., and 1N HCl (40 mL) and brine (30 mL) are added. The mixture is extracted with Et2O (3×50 mL), and the ethereal layers are back extracted with 1N NaOH (40 mL). The organic phase is dried (MgSO4), filtered and evaporated to a yellow oil. Kugelrohr distillation provides 3,3-dimethyl-7-tert-butyl-2,3-dihydrobenzo[b]thiophene as a colorless oil.

Aufarbeitung

  1. customby bubbling with N2 for 20 min
  2. temperatureThe solution is then heated under N2
  3. temperatureto reflux
  4. extractionThe mixture is extracted with Et2O (3×50 mL)
  5. extractionthe ethereal layers are back extracted with 1N NaOH (40 mL)
  6. dry with materialThe organic phase is dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated to a yellow oil
  9. distillationKugelrohr distillation

Quellen und Nachweise

ORD-Eintrag
ord-e06977f8af2744b9acf9f84ff78c9807
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05674891

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