3-Bromo-2-chloro-5-methylpyridine → 3-Bromo-2-ethoxy-5-methylpyridine

Temperatur

100 °C

To a solution of 3-bromo-2-chloro-5-methylpyridine (4.00 g, 19.37 mmol) in ethanol (100 mL) was added sodium ethoxide (6.59 g, 96.9 mmol) in three portions. The mixture was stirred under nitrogen at 100° C. for 2 days. The reaction was cooled to room temperature, diluted with water and extracted with DCM. The combined organic layers were dried (Na2SO4), and the solvent was removed under reduced pressure. Purification (FCC, SiO2, 20%, EtOAc/hexanes) afforded the title compound (3.00 g, 72%). 1H NMR (400 MHz, DMSO-d6) δ 7.94 (dd, J=0.8, 2.3 Hz, 1H), 7.89-7.82 (m, 1H), 4.31 (q, J=7.0 Hz, 2H), 2.18 (t, J=0.8 Hz, 3H), 1.30 (t, J=7.0 Hz, 3H).

1. temperatureThe reaction was cooled to room temperature
2. extractionextracted with DCM
3. dry with materialThe combined organic layers were dried (Na2SO4)
4. customthe solvent was removed under reduced pressure
5. customPurification (FCC, SiO2, 20%, EtOAc/hexanes)

ORD-Eintrag

ord-a5a5aff655ce452c83686e53b2305a94

Quelldatensatz

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09040692B2