Reaktion #340282

Reaktionsgleichung

I2

ethyl-5-bromonicotinate

Benzyl bromide

NaHCO3

→

title compound

Ethyl-5-benzylnicotinate

Lösungsmittel

DMA

EtOAc

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige(3-5 min)
2. 2
   Temperaturto cool to room temperature
3. 3
   SonstigeThe layers were separated
4. 4
   Extraktionthe aqueous layer was extracted with EtOAc (2×50 mL)
5. 5
   WaschenThe combined organic layers were sequentially washed with H2O (3×100 mL) and brine
6. 6
   Trocknenbefore being dried over Na2SO4
7. 7
   EinengenConcentration and purification by silica gel chromatography (hexane→50% EtOAc/hexane)

Vorschrift

A suspension of Zn (1.0 g, 15 mmol) and I2 (130 mg, 0.5 mmol) in DMA (15 mL) was stirred vigorously until the red color dissipated (3-5 min). Benzyl bromide (1.7 g, 10 mmol) was introduced and the resulting slurry was heated at 80° C. for 2.5 h at which point Cl2Pd(PPh3)2 (250 mg, 0.35 mmol) and a solution of ethyl-5-bromonicotinate (1.1 g, 5.0 mmol) in benzene (10 mL) were introduced and the reaction was heated at 80° C. for 1 h. The reaction was allowed to cool to room temperature and was diluted with EtOAc (100 mL). The mixture was poured into NaHCO3 (5% aqueous, 100 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×50 mL). The combined organic layers were sequentially washed with H2O (3×100 mL) and brine before being dried over Na2SO4. Concentration and purification by silica gel chromatography (hexane→50% EtOAc/hexane) provided the title compound as a brown oil. MS m/z: 242.1 (M+1).

Quelle