Ethyl 2-chloro-4-fluoro-5-nitrobenzoate → Ethyl 5-amino-2-chloro-4-fluorobenzoate

Temperature

40 °C

Then, 60 g of iron powder and 500 ml of 10% acetic acid were mixed, and the mixture was heated to 40° C. Separately, 50 g (0.20 mol) of ethyl 2-chloro-4-fluoro-5-nitrobenzoate was dissolved in a mixed solution of 20 ml of acetic acid and 20 ml of ethyl acetate, and added dropwise to the above iron powder-acetic acid mixed solution. Then, the reaction mixture was stirred at 50° C. for 1 hour and filtered though celite. The filtrate was extracted with 100 ml of ethyl acetate. The ethyl acetate layer was washed with aqueous sodium bicarbonate solution and saturated sodium chloride solution, and dried with magnesium sulfate. The solvent was distilled out, and the residue was purified by silica gel chromatography, which afforded to 40 g (0.18 mol) of ethyl 5-amino-2-chloro-4-fluorobenzoate.

1. filtrationfiltered though celite
2. extractionThe filtrate was extracted with 100 ml of ethyl acetate
3. washThe ethyl acetate layer was washed with aqueous sodium bicarbonate solution and saturated sodium chloride solution
4. dry with materialdried with magnesium sulfate
5. distillationThe solvent was distilled out
6. customthe residue was purified by silica gel chromatography, which

ORD record

ord-88ce6cdcdb584cb2b60debd3fa4ce442

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06703503B2