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

HRID 357718

Reaktionsgleichung

Reaktionsgleichung von HRID 357718
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-].[BrH:40].OO>ClCCl.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

7

Edukt 4

HCID 260Hydrogen BromideHCID 784Hydrogen PeroxideHCID 7219IndeneHCID 19153X 100

Produkt 1

HCID 820607(1R,2R)-2-bromo-2,3-dihydro-1H-inden-1-olAusbeute 83,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

237 ml of water, 173.9 g of indene (92 wt %; 1.38 mol), 2.8 g of Triton X-100 and 262.0 g of hydrogen bromide (47 wt %; 1.52 mol, 1.1 mol/mol indene) were put into a 1000-ml 3-mouthed flask, and emulsified by stirring together with a magnetic stirrer. The emulsion was stirred at 60° C. as 147.2 g of hydrogen peroxide (35 wt %; 1.52 mol, 1.1 mol/mol indene) was added dropwise over 4 hours and 20 minutes. After stirring for 2 hours at the same temperature, stirring was continued at room temperature overnight. 200 ml of dichloromethane was added to the reaction mixture, and after stirring at room temperature for 1 hour it was filtered at decreased pressure. The wet crystals were dried, to obtain 246.1 g of pale yellow crystals of trans-2-bromoindan-1-ol (yield 83.9%; GC purity 97.0%).

Aufarbeitung

  1. additionwas added dropwise over 4 hours and 20 minutes
  2. stirringAfter stirring for 2 hours at the same temperature
  3. stirringstirring
  4. stirringafter stirring at room temperature for 1 hour it
  5. filtrationwas filtered
  6. customThe wet crystals were dried

Quellen und Nachweise

ORD-Eintrag
ord-c5abfc27f6f04bc7ac0f09b592405472
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05841000

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