Acetic Acid → 4-Bromo-3-methyl-2-nitrophenol

Temperature

2.5 °C

A mixture of 10.0 g (53.5 mmol) of 4-bromo-3-methylphenol, 50 ml of acetic acid and 10 ml of water was stirred under cooling at 0 to 5° C. To the resulting mixture was dropwise added 3.71 g (58.8 mmol) of 70% nitric acid. After completion of the dropwise addition, the mixture was stirred at room temperature for about an hour. The reaction solution was then poured onto ice water. The mixture was extracted three times with diethyl ether. The combined extracts were washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 1.70 g (13.7%) of 4-bromo-3-methyl-2-nitrophenol.

1. additionAfter completion of the dropwise addition
2. stirringthe mixture was stirred at room temperature for about an hour
3. additionThe reaction solution was then poured onto ice water
4. extractionThe mixture was extracted three times with diethyl ether
5. washThe combined extracts were washed with water
6. dry with materialAfter drying over anhydrous magnesium sulfate
7. distillationthe solvent was distilled off under reduced pressure
8. customThe resulting residue was purified by silica gel column chromatography

ORD record

ord-a350131c08b34fc2a8daff9426a1fc00

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06248772B1