Acetic Acid → 4-Bromo-3-chloro-5-methylaniline

Temperature

100 °C

Iron (2.34 g, 41.8 mmol) and acetic acid (0.80 mL, 14.0 mmol) were added to a mixed solution of 2-bromo-1-chloro-3-methyl-5-nitro-benzene (3.50 g, 14.0 mmol) in ethanol (15 mL)-water (31 mL) at room temperature. The mixture was stirred at 100° C. for one hour, and a saturated aqueous sodium bicarbonate solution was then added at 0° C. The mixture was filtered through celite, and the filtrate was washed with ethyl acetate and water. The filtrate was concentrated under reduced pressure. Ethyl acetate was then added, and the organic layer and the aqueous layer were separated. The aqueous layer was repeatedly extracted with ethyl acetate three times, and the organic layers were then dried over sodium sulfate. The resulting residue was concentrated under reduced pressure to give 4-bromo-3-chloro-5-methyl-phenylamine as a pale brown solid (3.01 g, 98%).

1. filtrationThe mixture was filtered through celite
2. washthe filtrate was washed with ethyl acetate and water
3. concentrationThe filtrate was concentrated under reduced pressure
4. additionEthyl acetate was then added
5. customthe organic layer and the aqueous layer were separated
6. extractionThe aqueous layer was repeatedly extracted with ethyl acetate three times
7. dry with materialthe organic layers were then dried over sodium sulfate
8. concentrationThe resulting residue was concentrated under reduced pressure

ORD record

ord-2282d8a8bb24435a8e0969d8d7e249a5

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169254B2