Reaction #1509623

Reaction equation

2-Trichloroacetyl pyrrole

bromine

water

→

title compound 7

Yield 93.8%

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

Yield 93.8%

Solvents

chloroform

Conditions

Workup

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

Procedure

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