2-Bromo-1,3-dimethyl-4-nitrobenzene → 3-Bromo-2,4-dimethylaniline

2,6-Dimethyl-3-nitrobromo benzene (5.7 g, 0.025 mol) was dissolved in acetic acid (60 mL) and ethanol (60 mL). To this was added iron powder (5.6 g, 0.01 mol) in small portions and after the addition, it was refluxed for 2-3 h under nitrogen. An additional 2.8 g of iron powder was added and again refluxed for another 2 h. The mixture was filtered through celite and concentrated in vacuo. The residue was neutralized with sodium carbonate solution and repeatedly extracted (×3) with boiling ethyl acetate (50 mL each). Ethyl acetate was concentrated after drying over sodium sulfate to give a brown solid which was purified by chromatography on silica gel using 4% ethyl acetate in hexane to give a pale yellow solid.

1. additionafter the addition, it
2. temperaturewas refluxed for 2-3 h under nitrogen
3. temperatureagain refluxed for another 2 h
4. filtrationThe mixture was filtered through celite and
5. concentrationconcentrated in vacuo
6. extractionrepeatedly extracted (×3) with boiling ethyl acetate (50 mL each)
7. concentrationEthyl acetate was concentrated
8. dry with materialafter drying over sodium sulfate
9. customto give a brown solid which
10. customwas purified by chromatography on silica gel using 4% ethyl acetate in hexane
11. customto give a pale yellow solid

ORD record

ord-10aeef2ba255474a80d0ecd0952a79b6

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071609B2