Bromine → 2-Bromo-4-methoxy-5-methyl-indan-1-one

HRID 1099372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1099372
[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:13].[Br:14]Br.C(=O)(O)[O-].[Na+]>C(O)(=O)C.Br>[Br:14][CH:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:12])[C:3]=2[O:2][CH3:1])[C:7]1=[O:13]

Komponenten

6

Edukt 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 552973254-Methoxy-5-methyl-indan-1-one

Produkt 1

HCID 668127112-Bromo-4-methoxy-5-methyl-indan-1-oneAusbeute 44,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel2×HCID 260Hydrogen BromideLösungsmittel

Reaktionsbedingungen

Temperatur
22.5 °C

Versuchsvorschrift

To a stirred solution of 4-Methoxy-5-methyl-indan-1-one (5.0 gm, 0.0284 mole) in Acetic acid (65 ml) and Hydrobromic acid (1 ml), a solution of Bromine (1.47 ml, 0.0284 mole) in 5 ml Acetic acid was added at 10-20° C. The reaction mixture was stirred at 20-25° C. for an hour. Then it was poured into saturated solution of Sodium bicarbonate and extracted with Diethyl ether (3×100 ml). The organic layer was dried over Sodium sulphate, distilled under vacuum to give crude product which was purified over column chromatography using Ethyl acetate:Hexane (5:95) as a mobile phase. The collected fractions were distilled to give 3.2 gm of desired product as a viscous oil.

Aufarbeitung

  1. extractionextracted with Diethyl ether (3×100 ml)
  2. dry with materialThe organic layer was dried over Sodium sulphate
  3. distillationdistilled under vacuum
  4. customto give crude product which
  5. customwas purified over column chromatography
  6. distillationThe collected fractions were distilled

Quellen und Nachweise

ORD-Eintrag
ord-2ca390011412433cafd18cc4fdc18ff4
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143424B2

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