Réaction #1509623

Équation de réaction

2-Trichloroacetyl pyrrole

bromine

water

→

title compound 7

Rendement 93.8%

1-(4-bromo-1H-pyrrol-2-yl)-2,2,2-trichloro-ethanone

Rendement 93.8%

Solvants

chloroform

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONOnce addition
2. 2
   Extractionextracted with chloroform (3×20 mL) The combined organic layers
3. 3
   Lavagewere washed with sat. NaHCO3 (2×30 mL), brine (1×20 mL)
4. 4
   Séchagedried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Autreevaporated to dryness
7. 7
   AutrePurification of the residue by column chromatography (Hexanes/Diethyl Ether 95:5)

Mode opératoire

2-Trichloroacetyl pyrrole 6 (5.00 g, 23.3 mmol) was dissolved in anhydrous chloroform (20 mL) The solution was cooled to −10° C. before the drop-wise addition of bromine (1.20 mL, 23.3 mmol) to the flask. Once addition was complete the reaction was allowed to warm to room temperature on its own accord while stirring for an additional 30 minutes. The reaction was poured into water (40 mL) and extracted with chloroform (3×20 mL) The combined organic layers were washed with sat. NaHCO3 (2×30 mL), brine (1×20 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to dryness. Purification of the residue by column chromatography (Hexanes/Diethyl Ether 95:5) yielded the title compound 7 (6.37 g, 93%) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 12.86 (s, 1H), 7.54 (s, 1H), 7.32 (s, 1H); 13C NMR (100 MHz, DMSO-d6) δ 171.67, 129.06, 122.01, 121.54, 97.60, 94.56; HRMS (FAB) calcd for C6H3BrCl3NO (M+) 288.8464, found 288.8479.

Source