Reaktion #2507874

Reaktionsgleichung

Na2CO3

4-chlorophenyl boronic acid

DMF

methyl 4-bromo-1H-pyrrole-2-carboxylate

→

product

Ausbeute 25.0%

methyl 4-(4-chlorophenyl)-1H-pyrrole-2-carboxylate

Ausbeute 25.0%

Lösungsmittel

water

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was degassed, with Ar
2. 2
   TemperaturAfter cooling
3. 3
   Sonstigethe reaction to RT
4. 4
   ExtraktionThe aqueous layer was extracted, with EtOAc (3×20 mL)
5. 5
   Trocknendried over Na2SO4, and cone, in vacuo
6. 6
   Sonstigeto yield a brown oil
7. 7
   SonstigeThe oil was purified by column chromatography (silica gel, 0%-15% gradient elution with EtOAc/hexanes)

Vorschrift

To a stirred DMF solution (40 mL) containing methyl 4-bromo-1H-pyrrole-2-carboxylate (1.0 g, 4.9 mmol), commercially available from Bionet, and Pd(Ph3)4 (195 mg, 0.17 mmol) was added Na2CO3 (1.3 g, 12.52 mmol) (dissolved in minimum amount water) and 4-chlorophenyl boronic acid (0.85 g, 5.43 mmol) under Ar. The mixture was degassed, with Ar prior to stirring overnight at 110° C. After cooling the reaction to RT, it was diluted with 10 mL of water and 200 mL of EtOAc. The aqueous layer was extracted, with EtOAc (3×20 mL). The organic layers were combined, dried over Na2SO4, and cone, in vacuo to yield a brown oil. The oil was purified by column chromatography (silica gel, 0%-15% gradient elution with EtOAc/hexanes) to yield 288 mg (25%) of product as white solid. MS (ESI) 236 (M+H)+.

Quelle