2-Methylbenzenesulfonic acid → 1H-Indene, 2-bromo-

HRID 11963

Reaktionsgleichung

Reaktionsgleichung von HRID 11963
[Br:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1O.C1(C)C(S(O)(=O)=O)=CC=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH2:10][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Komponenten

4

Edukt 2

HCID 69252-Methylbenzenesulfonic acidHCID 820607(1R,2R)-2-bromo-2,3-dihydro-1H-inden-1-ol

Produkt 1

HCID 5755861H-Indene, 2-bromo-Ausbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A 500 mL flask was charged with 25.5 g (120 mmol) of trans-2-bromo-1-indanol, 1 g of toluenesulfonic acid and 350 mL of toluene. This was capped with a Dean-Stark trap and heated to reflux for two hours at which time the system was cooled to room temperature and the volatiles removed in vacuo to leave a dark oil. The residue was taken up into hexanes and eluted through a silica pad using hexanes. Removal of the volatiles in vacuo gave 22.5 g (96 percent) of a light yellow oil.

Aufarbeitung

  1. customThis was capped with a Dean-Stark trap
  2. temperatureheated
  3. temperatureto reflux for two hours at which time the system
  4. customthe volatiles removed in vacuo
  5. customto leave a dark oil
  6. washeluted through a silica pad
  7. customRemoval of the volatiles in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1c7e89d4d4514972a067ddc65a248326
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098356B2

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