Lithium iodide → 3-Chloro-5-hydroxybenzonitrile

Temperature

170 °C

step 2—A 250 flask was charged with 5-chloro-3-methoxy-benzonitrile (7.0 g, 41.766 mmol) and 2,4,6-collidine (100 mL). The mixture was heated to 170° C. and LiI (16.76 g, 125.298 mmol) was added and the reaction mixture was heated for 4 h. When the methyl ether was consumed the reaction was cooled to RT and quenched with 10% aqueous HCl. The resulting mixture was extracted with EtOAc and washed with water and brine. The EtOAc extract was dried over (Na2SO4) and filtered. The solvent was removed in vacuo to afford a yellow oil which was purified by silica gel chromatography eluting with EtOAc/hexane (10:90) to afford 6.0 g (94%) of 3-chloro-5-hydroxy-benzonitrile.

1. temperaturethe reaction mixture was heated for 4 h
2. customWhen the methyl ether was consumed the reaction
3. temperaturewas cooled to RT
4. customquenched with 10% aqueous HCl
5. extractionThe resulting mixture was extracted with EtOAc
6. washwashed with water and brine
7. extractionThe EtOAc extract
8. dry with materialwas dried over (Na2SO4)
9. filtrationfiltered
10. customThe solvent was removed in vacuo
11. customto afford a yellow oil which
12. customwas purified by silica gel chromatography
13. washeluting with EtOAc/hexane (10:90)

ORD record

ord-0923bdfec24a4d65ba9c9028f97a027b

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08026362B2