Reaktion #217665

Reaktionsgleichung

ketone

N-(4-Acetyl-phenyl)-4-trifluoromethoxy-benzenesulfonamide

phenyltrimethylammonium tribromide

water

→

N-[4-(2-Bromo-acetyl)-phenyl]-4-trifluoromethoxy-benzenesulfonamide

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 (90% desired mono-brominated material by LC-MS, 5%

Vorschrift

The ketone from step 1 (0.32 g, 0.868 mmol) was dissolved in THF (9 ml), and phenyltrimethylammonium tribromide (PTT) (0.368 g, 0.868 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 (90% desired mono-brominated material by LC-MS, 5% starting material, 5% dibrominated) suitable for the next step. LC-MS (ES−): 436, 438 m/e.

Quelle