반응 #56873

반응 방정식

hydrobromic acid

sodium nitrite

3-iodo-4-methyl-phenylamine

hydrobromic acid

→

5-bromo-2-methyl-1-iodo-benzene

수율 71.0%

용매

water

water

반응 조건

후처리

1. 1
   온도After cooling in an ice bath
2. 2
   온도cooled in an ice bath
3. 3
   workup.STIRRINGAfter stirring for 20 minutes
4. 4
   온도the mixture was heated at 90° C. for 1 hour
5. 5
   workup.STIRRINGAfter stirring at room temperature for 16 hours
6. 6
   추출extracted with dichloromethane (100 ml)
7. 7
   세척The organic layer was washed with saturated aqueous sodium bicarbonate solution (100 ml)
8. 8
   세척washed with saturated aqueous sodium chloride solution (100 ml)
9. 9
   건조dried over magnesium sulfate
10. 10
    농축concentrated under reduced pressure
11. 11
    기타The residue was purified by flash chromatography
12. 12
    세척eluting with hexane

실험 절차

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).

출처