Water → 6-Bromo-3-isopropoxy-2-methylpyridine

Temperatur

100 °C

6-Bromo-2-methylpyridin-3-ol (10.5 g, 55.9 mmol) was dissolved in DMF (100 mL). K2CO3 (19.3 g, 139.6 mmol) and 2-bromopropane (13.1 ml, 139.6 mmol) were added to the solution and the reaction mixture was heated at 100° C. overnight. The reaction mixture was poured onto a mixture of water and EtOAc (200 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×). The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The crude oil was purified by silica gel column chromatography (0-20% ethyl acetate/heptanes) to give 6-bromo-3-isopropoxy-2-methylpyridine (10.9 g, 85%) as a yellow oil. 1H-NMR (300 MHz, CDCl3) 1.42 (d, 6H), 2.48 (s, 3H), 4.65 (m, 1H), 7.20 (d, 1H), 8.04 (d, 1H).

1. customThe layers were separated
2. extractionthe aqueous layer was extracted with EtOAc (2×)
3. dry with materialThe combined organic layers were dried (Na2SO4)
4. concentrationconcentrated in vacuo
5. customThe crude oil was purified by silica gel column chromatography (0-20% ethyl acetate/heptanes)

ORD-Eintrag

ord-4230d3130cd940e6a25e34a934d55773

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08828996B2