Indene → (1R,2R)-2-bromo-2,3-dihydro-1H-inden-1-ol

HRID 357719

Reaktionsgleichung

Reaktionsgleichung von HRID 357719
C1C2C(=CC=CC=2)C=C1.CCC(C[O:16][C:17](C(N(CC[NH+](C)C)C)=O)([C:24]1[CH:29]=CC=CC=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)CC.[Cl-].[Br:40]Br>O>[Br:40][C@@H:24]1[CH2:29][C:19]2[C:18](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:17]1[OH:16]

Komponenten

5

Edukt 3

HCID 7219IndeneHCID 19153X 100HCID 24408Bromine

Produkt 1

HCID 820607(1R,2R)-2-bromo-2,3-dihydro-1H-inden-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

43.5 g of indene (92 wt %; 0.345 mol), 0.7 g of Triton X-100 and 100 ml of water were put into a 500-ml 3-mouthed flask, and mixed by stirring. Mixing was continued at 60° C. as 27.5 g of bromine (0.172 mol, 0.5 mol/mol of indene) was added dropwise over approximately 3 hours. After this, stirring at 60° C. was continued. The reaction mixture was extracted with ethyl acetate directly after dropwise addition of bromine, and after mixing for a further 1 hour. Yields of trans-2-bromoindan-1-ol were calculated from the hydrogen bromide concentrations in the aqueous phase (by gravimetric titration using silver nitrate), and the quantity of indene in the extraction layer was found by GC by means of a calibration line and used to calculate percent conversion.

Aufarbeitung

  1. additionmixed
  2. additionMixing
  3. additionwas added dropwise over approximately 3 hours
  4. stirringAfter this, stirring at 60° C.
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. additiondirectly after dropwise addition of bromine
  7. additionafter mixing for a further 1 hour

Quellen und Nachweise

ORD-Eintrag
ord-5e3b608a02844ee681a9b9028f921b75
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05841000

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