Hydrochloric Acid → 5-Iodosalicylaldehyde

To the mixture of 20 g (91 mmol) of 4-iodophenol and 25.1 g (264 mmol) anhydrous magnesium dichloride in 455 mL of anhydrous acetonitrile was added triethylamine and paraformaldehyde. The mixture was heated to reflux for 4 h, allowed to cool to rt and treated with 500 mL of 5% HCl. The solution was extracted three times with EtOAc. The combined organic extracts were washed with brine (3×) and dried over anhydrous magnesium sulfate. The dried organic solution was evaporated to afford an oil, which was purified by silica gel chromatography with EtOAc/hexane (2:8). Concentration of the desired fractions afforded 15 g (66%) of a yellow solid, which was used directly in the next step without further purification.

1. temperatureThe mixture was heated
2. temperatureto reflux for 4 h
3. extractionThe solution was extracted three times with EtOAc
4. washThe combined organic extracts were washed with brine (3×)
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe dried organic solution was evaporated
7. customto afford an oil, which
8. customwas purified by silica gel chromatography with EtOAc/hexane (2:8)

ORD record

ord-44b9b69dd211428cb9625651ec2da0cd

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07259266B2