Sodium methanethiolate → 4-Bromo-5-hydroxy-2,3-dihydro-1H-inden-1-one

HRID 471435Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471435
[Br:1][C:2]1[C:10]([O:11]C)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:13].C[S-].[Na+]>CN(C)C=O>[Br:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:13]

Komponenten

4

Edukt 2

HCID 4378561Sodium methanethiolateHCID 378189874-bromo-5-methoxy-2,3-dihydro-1H-inden-1-one

Produkt 1

HCID 688667904-Bromo-5-hydroxy-2,3-dihydro-1H-inden-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

4-Bromo-5-methoxy-indane-1-one (10 g, 41.48 mmol) and sodium methane-thiolate (12.68 g, 180.94 mmol) are dissolved in 25 mL of N,N-dimethylformamide and the reaction mixture is stirred at 120° C. for 3 h. The reaction mixture is concentrated under vacuum, 40 mL of a 2 M solution of hydrochloric acid is added and the reaction mixture is extracted with 300 mL of ethyl acetate. The organic phase is collected, dried over sodium sulfate and concentrated under vacuum. The crude product obtained (9 g) is used in the next step without any further treatment.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated under vacuum, 40 mL of a 2 M solution of hydrochloric acid
  2. additionis added
  3. extractionthe reaction mixture is extracted with 300 mL of ethyl acetate
  4. customThe organic phase is collected
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ed0a5ff54fe34080a8f4a48370d79a39
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633182B2

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