3-(4-Bromophenyl)propionic acid → 1-Indanone, 6-bromo-

HRID 472953

Reaktionsgleichung

Reaktionsgleichung von HRID 472953
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-]>O=S(Cl)Cl.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:8][CH2:9][C:10]2=[O:12])=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 27356093-(4-Bromophenyl)propionic acidHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 1397781-Indanone, 6-bromo-Ausbeute 473,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

A mixture of 3-(4-bromophenyl)propanoic acid (26 g, 12 mmol) in SOCl2 (50 mL) was refluxed overnight, the mixture was concentrated, then added to AlCl3 (80 g, 61 mmol) in DCM (100 mL), the mixture was stirred at room temperature overnight. The mixture was quenched with HCl aqueous, extracted with DCM, washed with brine, dried over Na2SO4, concentrated to give 6-bromo-indan-1-one (12 g, 48%). 1H-NMR (CD3OD): 2.65 (m, 2H), 3.06 (m, 2H), 7.31 (m, 1H), 7.62 (m, 1H), 7.80 (m, 1H).

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. concentrationthe mixture was concentrated
  3. customThe mixture was quenched with HCl aqueous
  4. extractionextracted with DCM
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-048863f3e19545faafea1de964a80668
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633212B2

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