Hydrochloric Acid → 4-Chloro-2-[3-hydroxy-5-(hydroxymethyl)phenoxy]benzonitrile

Temperature

120 °C

To a stirred solution of cesium carbonate (11.62 g) in dry DMF (70 ml) was added 5-(hydroxymethyl)-1,3-benzenediol (5 g) followed by 4-chloro-2-fluorobenzonitrile (5 g). The mixture was then stirred and heated at 120° C. for 3 h. The cooled mixture was then poured into water (200 ml) and made acidic by the addition of 2M aqueous hydrochloric acid The products were extracted into ethyl acetate (3×150 ml), and the combined extracts were washed with 10% aqueous potassium carbonate solution (100 ml). The organic extract was collected, dried (MgSO4) and concentrated to dryness. Diethyl ether was added to the residue and the mixture filtered. The filtrate was concentrated to dryness and the residue purified by chromatography (silica, 70% diethyl ether/isohexane) to afford, after trituration with diethyl ether, the sub-title compound (800 mg).

1. extractionwere extracted into ethyl acetate (3×150 ml)
2. washthe combined extracts were washed with 10% aqueous potassium carbonate solution (100 ml)
3. extractionThe organic extract
4. customwas collected
5. dry with materialdried (MgSO4)
6. concentrationconcentrated to dryness
7. additionDiethyl ether was added to the residue
8. filtrationthe mixture filtered
9. concentrationThe filtrate was concentrated to dryness
10. customthe residue purified by chromatography (silica, 70% diethyl ether/isohexane)
11. customto afford

ORD record

ord-72539a16a7374c18adf0cfd1f63cd558

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07119122B2