Sulfuric Acid → 4-Bromo-1H-indene

HRID 923727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 923727
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2O.S(=O)(=O)(O)O>O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][CH2:6]2

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 133302084-Bromo-1-indanol

Produkt 1

HCID 156376244-Bromo-1H-indeneAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Compound 3 (150 g, 704 mmol, 1 equiv) was suspended in a mixture of concentrated sulfuric acid (250 mL) and water (1.25 L). The mixture was refluxed overnight. The reaction was cooled and extracted with 1.5 L of dichloromethane. The organic layer was washed with saturated sodium bicarbonate (1.5 L), dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified over silica gel (800 g), eluting with heptanes to give compound 4 (95 g, 69% yield) as a light yellow oil.

Aufarbeitung

  1. temperatureThe mixture was refluxed overnight
  2. temperatureThe reaction was cooled
  3. extractionextracted with 1.5 L of dichloromethane
  4. washThe organic layer was washed with saturated sodium bicarbonate (1.5 L)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified over silica gel (800 g)
  8. washeluting with heptanes

Quellen und Nachweise

ORD-Eintrag
ord-7371366b6cdc45b1a106c376406acbfa
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09279024B2

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