Acetic Acid → Ethyl 2-(4,5-dichloro-2-hydroxyphenylamino)acetate

To a solution of 2-amino-4,5-dichlorophenol (2.0 g, 11.3 mmol) and ethyl-2-oxoacetate (2.26 g, 12.42 mmol) in DCM (50 mL) at room temperature, AcOH (1 mL) was added and the resulting mixture was stirred for 1 h. To this mixture, NaBH(OAc)3 (7.2 g, 33.9 mmol) was added and then stirred for 16 h. The mixture was concentrated in vacuo and the residue was suspended in DCM. The mixture was filtered through a pad of Celite and the filtrate was washed with brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=10:1) to afford the desired product (2.4 g, 81% yield) as a solid.

1. stirringstirred for 16 h
2. concentrationThe mixture was concentrated in vacuo
3. filtrationThe mixture was filtered through a pad of Celite
4. washthe filtrate was washed with brine
5. dry with materialThe organic layer was dried over anhydrous Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=10:1)

ORD record

ord-0b276b5a9d03459dbf4f44630f146cfb

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09227978B2