Bromine → 4-Bromo-6-isopropyl-2-methyl-5-(pentafluorophenoxy)indan-1-one

HRID 716449Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 716449
[Al+3].[Cl-].[Cl-].[Cl-].[CH:5]([C:8]1[CH:16]=[C:15]2[C:11]([CH2:12][CH:13]([CH3:18])[C:14]2=[O:17])=[CH:10][C:9]=1[O:19][C:20]1[C:25]([F:26])=[C:24]([F:27])[C:23]([F:28])=[C:22]([F:29])[C:21]=1[F:30])([CH3:7])[CH3:6].[Br:31]Br>ClCCl.[O-]S([O-])=O.[Na+].[Na+]>[Br:31][C:10]1[C:9]([O:19][C:20]2[C:21]([F:30])=[C:22]([F:29])[C:23]([F:28])=[C:24]([F:27])[C:25]=2[F:26])=[C:8]([CH:5]([CH3:6])[CH3:7])[CH:16]=[C:15]2[C:11]=1[CH2:12][CH:13]([CH3:18])[C:14]2=[O:17]

Komponenten

6

Edukt 3

HCID 24408BromineHCID 6451240Aluminum(III) ChlorideHCID 893924646-Isopropyl-2-methyl-5-(pentafluorophenoxy)indan-1-one

Produkt 1

HCID 893924444-Bromo-6-isopropyl-2-methyl-5-(pentafluorophenoxy)indan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 24437Sodium SulfiteLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 17.5 g (131 mmol) of AlCl3 in 28 ml of dichloromethane cooled to −20° C. a solution of 32.4 g (87.5 mmol) of 6-isopropyl-2-methyl-5-(pentafluorophenoxy)indan-1-one in 46 ml of dichloromethane was added dropwise. Further on, this solution was warmed to 0° C., and 4.80 ml (96.0 mmol) of bromine was added dropwise by vigorous stirring for 0.5 h. This mixture was stirred for 24 h at room temperature and then poured in cold aqueous Na2SO3 to remove an excess of bromine. The product was extracted with 3×50 ml of dichloromethane. The combined extract was evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: n-hexane-dichloromethane-ether 50:50:1, vol.). Yield 20.1 g (51%). Additionally, 15.0 g of the starting indanone was recovered.

Aufarbeitung

  1. additionwas added dropwise
  2. stirringThis mixture was stirred for 24 h at room temperature
  3. customto remove an excess of bromine
  4. extractionThe product was extracted with 3×50 ml of dichloromethane
  5. extractionThe combined extract
  6. customwas evaporated to dryness
  7. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: n-hexane-dichloromethane-ether 50:50:1, vol.)
  8. customAdditionally, 15.0 g of the starting indanone was recovered

Quellen und Nachweise

ORD-Eintrag
ord-4c0941602d3140a1a6ce9aacc15cbeed
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187583B2

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