Bromine → HCID 54426727, compound

Temperature

30 °C

Iron powder (0.5 g) and iodine (0.05 g) were added to a solution of 2-chloro-6-(methylsulphenyl)benzonitrile (10.0 g) in a mixture of carbon tetrachloride and dichloromethane. The mixture was warmed to 30° C. and bromine (9.5 g) was added. The mixture was heated at 55° C. for 5 hours. It was cooled, washed with aqueous sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was redissolved in a mixture of carbon tetrachloride and dichloromethane and treated with iron powder (0.5 g) and iodine (0.05 g). Bromine (6.5 g) was added and the mixture was heated at 55° C. for 5 hours. It was cooled and washed with sodium bisulphite, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane to give 3-bromo-2-chloro-6-(methylsulphenyl)benzonitrile (6.51 g) as an orange solid NMR (CDCl3) 2.5(s,3H) 7.0(d, 1H) 7.65(d, 1H).

1. temperatureThe mixture was heated at 55° C. for 5 hours
2. temperatureIt was cooled
3. washwashed with aqueous sodium bisulphite, water
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. customThe filtrate was evaporated to dryness
7. dissolutionthe residue was redissolved in a mixture of carbon tetrachloride and dichloromethane
8. additiontreated with iron powder (0.5 g) and iodine (0.05 g)
9. additionBromine (6.5 g) was added
10. temperaturethe mixture was heated at 55° C. for 5 hours
11. temperatureIt was cooled
12. washwashed with sodium bisulphite, water
13. dry with materialdried (MgSO4)
14. filtrationfiltered
15. customThe filtrate was evaporated to dryness
16. customthe residue was purified by column chromatography
17. washeluted with a mixture of ethyl acetate and n-hexane

ORD record

ord-eb5637631813478ea6f5c16f86581de6

Source dataset

uspto-grants-1997_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05656573