Potassium Carbonate → 2-(4-chlorophenyl)-5-nitropyridine

Temperatur

100 °C

A flask was charged with 2-bromo-5-nitropyridine (4 g, 19.71 mmol), 4-chlorophenylboronic acid (4.54 g, 27.6 mmol), Pd(PPh3)4 (1.139 g, 0.985 mmol), potassium carbonate (8.16 g, 59.1 mmol), dioxane (40 ml) and water (20 ml) at room temperature. The flask was sealed, flushed with nitrogen for three times and heated at 100° C. for 3 hours. The reaction mixture was diluted with EtOAc (100 ml) and filtered. The filtrate was concentrated. The residue was washed with water by filtration. The afforded solid was dissolved in EtOAc (200 ml) and washed with saturated aqueous sodium bicarbonate solution and brine, dried over Na2SO4, concentrated, and dried under vacuum to afford crude 2-(4-chlorophenyl)-5-nitropyridine (4.8 g, 75% purity, 78% yield) as yellow solid. 1H NMR (400 MHz, DMSO-d6) ppm 7.27-7.36 (m, 4H) 7.51-7.61 (m, 3H).

1. customThe flask was sealed
2. customflushed with nitrogen for three times
3. additionThe reaction mixture was diluted with EtOAc (100 ml)
4. filtrationfiltered
5. concentrationThe filtrate was concentrated
6. washThe residue was washed with water by filtration
7. dissolutionThe afforded solid was dissolved in EtOAc (200 ml)
8. washwashed with saturated aqueous sodium bicarbonate solution and brine
9. dry with materialdried over Na2SO4
10. concentrationconcentrated
11. customdried under vacuum

ORD-Eintrag

ord-f462997f79f64c07b3aa1a5a22c5e1d5

Quelldatensatz

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08993619B2