반응 #733448

반응 방정식

hexane

1-bromo-3-ethynylbenzene

triethylamine

4-iodo-1H-pyrrole-2-carbaldehyde

→

title compound

수율 93.5%

4-[(3-Bromophenyl)ethynyl]-1H-pyrrole-2-carbaldehyde

수율 93.5%

용매

water

DMF

ethyl acetate

반응 조건

후처리

1. 1
   workup.ADDITIONThen the following were added
2. 2
   추출the organic material was extracted into dichloromethane
3. 3
   세척The organic extracts were washed with water and brine
4. 4
   건조dried over MgSO4
5. 5
   여과filtered
6. 6
   기타evaporated
7. 7
   기타The residue was chromatographed on silica gel using 3:1 hexane

실험 절차

A solution of 4-iodo-1H-pyrrole-2-carbaldehyde (0.50 g; 2.262 mmol) and bis(triphenylphosphine)palladium-(II)chloride (0.079 g; 0.113 mmol)) in DMF (15 mL; degassed with nitrogen for 30 minutes) was stirred at ambient temperature for 15 minutes. Then the following were added: 1-bromo-3-ethynylbenzene (0.61 g; 3.394 mmol), copper iodide (43 mg; 0.226), and triethylamine (1.58 mL, 11.3 mmol). The course of the reaction was followed with TLC (4:1, hexane:ethyl acetate). After 2 hours the reaction mixture was diluted with water and the organic material was extracted into dichloromethane. The organic extracts were washed with water and brine, dried over MgSO4, filtered, and evaporated. The residue was chromatographed on silica gel using 3:1 hexane:ethyl acetate to yield 0.58 g (93%) of the title compound as a yellow crystalline solid, mp 152-156° C.; MS (ES) m/z 272.0, [M−H]−.

출처