Reaktion #217669

Reaktionsgleichung

ketone

1-(1-Benzenesulfonyl-2,3-dihydro-1H-indol-5-yl)-ethanone

phenyltrimethylammonium tribromide

water

→

1-(1-Benzenesulfonyl-2,3-dihydro-1H-indol-5-yl)-2-bromo-ethanone

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeleaving an orange solution which
2. 2
   workup.ADDITIONwas added
3. 3
   SonstigeTHF was then evaporated
4. 4
   Extraktionthe resulting aqueous mixture was extracted with ethyl acetate
5. 5
   TrocknenDrying over Na2SO4 and evaporation
6. 6
   Sonstigeleaves a white crystalline solid (85% desired mono-brominated material by LC-MS, 5%

Vorschrift

The ketone from step 1 (0.310 g, 1.02 mmol) was dissolved in THF (3 ml), and phenyltrimethylammonium tribromide (PTT) (0.386 g, 1.02 mmol) was added as a solid leaving an orange solution which began to deposit a white solid immediately. Stirring for 1.5 hours leaves a colorless mixture to which water (5 ml) was added. THF was then evaporated and the resulting aqueous mixture was extracted with ethyl acetate. Drying over Na2SO4 and evaporation leaves a white crystalline solid (85% desired mono-brominated material by LC-MS, 5% starting material, 10% dibrominated) suitable for the next step. LC-MS (ES+): 381, 379 m/e.

Quelle