Hydrochloric Acid → 2-Amino-4-chloro-5-fluorobenzaldehyde

A mixture of 4-chloro-5-fluoro-2-nitrobenzaldehyde (1.50 g, 7.37 mmol), concentrated hydrochloric acid (0.30 ml, 3.68 mmol), and iron (1.32 g, 23.6 mmol) in EtOH (18 mL), AcOH (18 mL), and water (9 mL) was heated to reflux for 30 minutes, then cooled to RT. The resulting suspension was filtered through CELITE™ and the filtrate was then partitioned between EtOAc and water. The layers were separated, the organic layer was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give 2-amino-4-chloro-5-fluorobenzaldehyde as a yellow solid (1.15 g, 90% yield). m/z=174 (M+1).

1. temperaturewas heated
2. temperatureto reflux for 30 minutes
3. filtrationThe resulting suspension was filtered through CELITE™
4. customthe filtrate was then partitioned between EtOAc and water
5. customThe layers were separated
6. washthe organic layer was washed with saturated aqueous sodium bicarbonate solution
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-14e0cabaf2704a7aaf2b60e220870ced

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691986B2