Reaktion #56873
ord-ad06025d2155485499bc7d8dc4f3f193
Reaktionsgleichung
Reagenzien
Reaktionsbedingungen
Aufarbeitung
- 1TemperaturAfter cooling in an ice bath
- 2Temperaturcooled in an ice bath
- 3workup.STIRRINGAfter stirring for 20 minutes
- 4Temperaturthe mixture was heated at 90° C. for 1 hour
- 5workup.STIRRINGAfter stirring at room temperature for 16 hours
- 6Extraktionextracted with dichloromethane (100 ml)
- 7WaschenThe organic layer was washed with saturated aqueous sodium bicarbonate solution (100 ml)
- 8Waschenwashed with saturated aqueous sodium chloride solution (100 ml)
- 9Trocknendried over magnesium sulfate
- 10Einengenconcentrated under reduced pressure
- 11SonstigeThe residue was purified by flash chromatography
- 12Wascheneluting with hexane
Vorschrift
A mixture of 3-iodo-4-methyl-phenylamine (5.0 g, 21 mmol) and 48% hydrobromic acid (30 ml) was heated at 90° C. for 30 minutes. After cooling in an ice bath, a solution of sodium nitrite (1.7 g, 25.2 mmol) in water (5 ml) was added and stirred for 15 minute. This mixture was added to a mixture of copper bromide (I) (3.6 g, 25.2 mmol), 48% hydrobromic acid (20 ml) and ice (50 g) cooled in an ice bath. After stirring for 20 minutes, the mixture was heated at 90° C. for 1 hour. After stirring at room temperature for 16 hours, the mixture was treated with water (350 ml) and extracted with dichloromethane (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution (100 ml), washed with saturated aqueous sodium chloride solution (100 ml), dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with hexane to give 5-bromo-2-methyl-1-iodo-benzene (4.4 g, 71% yield). 1H NMR (acetone-d6) δ 2.40 (s, 3H, CH3), 7.30 (d, 1H, J=8.2 Hz, Ar), 7.50 (dd, 1H, J=8.2 Hz, J=2.0 Hz, Ar), 8.00 (d, 1H, J=2.0 Hz, Ar).