Dichloromethane → 4,5-Dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

HRID 1699746Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1699746
[Br:1][C:2]1[C:10]([CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:9][C:5]2[CH2:6][CH2:7][O:8][C:4]=2[C:3]=1[Br:16].ClCCl.S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>CN(C)C=O.CO>[Br:16][C:3]1[C:4]2[O:8][CH2:7][CH2:6][C:5]=2[C:9]2[C:13](=[O:15])[CH2:12][CH2:11][C:10]=2[C:2]=1[Br:1]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 110245373-(6,7-dibromo-2,3-dihydrobenzofuran-5-yl)propanoic Acid

Produkt 1

HCID 117272814,5-Dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-oneAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 3-(6,7-dibromo-2,3-dihydrobenzofuran-5-yl)propionic acid (10.0 g, 28.6 mmols), dichloromethane (35 mL), thionyl chloride (5.11 g, 40.8 mmols) and N,N-dimethylformamide (30 mg) was heated to reflux for 1 hour. After cooling, aluminum chloride (4.66 g, 43.3 mmols) was added to the reaction mixture a trot more than 0° C. and then the mixture was stirred for 30 min. The reaction mixture was poured into precooled methanol (200 mL), then stirred for 30 min. Crystals precipitated were collected by filtration, washed with water (500 mL) followed by methanol (500 mL) to obtain 7.9 g (yield: 89%) of the title compound.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling
  4. stirringstirred for 30 min
  5. customCrystals precipitated
  6. filtrationwere collected by filtration
  7. washwashed with water (500 mL)

Quellen und Nachweise

ORD-Eintrag
ord-48d5da54d39348e8b7e85b4cdf353cf7
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06348485B1

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