1-Bromo-3-chloropropane → 2-Chloro-4-(3-chloro-propoxy)-benzaldehyde

Temperatur

65 °C

1-Bromo-3-chloropropane (2.55 g, 16.2 mmol, 1.0 equiv) was added to a solution of 2-chloro-4-hydroxybenzaldehyde (2.54 g, 16.2 mmol) and K2CO3 (4.48 g, 32.4 mmol) in acetonitrile (41 mL). The mixture was heated at 65° C. for 18 h, then cooled to room temperature (rt) and filtered through diatomaceous earth. The filtrate was concentrated to yield the crude product, which was purified by column chromatography (silica gel, 5% EtOAc in hexanes) to afford 3.19 g of a colorless oil (66%). 1H NMR (400 MHz, CD3OD): 10.3 (s, 1H), 7.87 (d, J=8.0, 1H), 7.10 (d, J=4.0, 1H), 7.03 (dd, J=8.0, 4.0, 1H), 4.23 (t, J=8.0, 2H), 3.76 (t, J=8.0, 2H), 2.31-2.22 (m, 2H).

1. temperaturecooled to room temperature (rt)
2. filtrationfiltered through diatomaceous earth
3. concentrationThe filtrate was concentrated
4. customto yield the crude product, which
5. customwas purified by column chromatography (silica gel, 5% EtOAc in hexanes)

ORD-Eintrag

ord-312364090d3644958e9d920eb3b0a2ba

Quelldatensatz

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07956066B2