Methyl iodide → Benzene, 1-bromo-2,4-dimethyl-5-(methylsulfonyl)-

HRID 2082581Notes

Reaction equation

HRID 2082581 reaction equation
Cl[S:2]([OH:5])(=O)=[O:3].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[CH3:14].[C:15](=O)([O-])[O-].[Na+].[Na+].S([O-])([O-])=O.[Na+].[Na+].CI>O.C(Cl)CCl>[Br:6][C:7]1[CH:12]=[C:11]([S:2]([CH3:15])(=[O:5])=[O:3])[C:10]([CH3:13])=[CH:9][C:8]=1[CH3:14]

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 24437Sodium SulfiteHCID 24638Chlorosulfonic acidHCID 68503Benzene, 1-bromo-2,4-dimethyl-

Product 1

HCID 10945260Benzene, 1-bromo-2,4-dimethyl-5-(methylsulfonyl)-

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent4×HCID 962WaterSolvent2×

Procedure

6 g of common salt was added to 25 ml of 1,2-dichloroethane (EDC), and 40 g of chlorosulfonic acid was added dropwise thereto at room temperature under stirring and 20 ml of EDC was further added thereto. To the resultant mixture, was dropwise added 18.5 g (0.1 mol) of 4-bromo-m-xylene at room temperature over one hour period. After dropwise added, the resultant mixture was stirred continuously for 30 minutes, and was then heated to 70° C., and was stirred continuously for one hour, and was thereafter standed to cool to room temperature. After dropping the resultant reaction liquor to 65 ml of water, the mixture was stirred for 30 minutes and EDC layer was taken out. To a solution having 17 g of sodium carbonate and 13 g of sodium sulfite dissolved in 85 ml of water, was dropwise added the EDC layer thus obtained at 65° C. over one hour period, and the resultant mixture was stirred at the same temperature for 4 hours to take the aqueous layer out. 14.2 g of methyl iodide was added dropwise to the aqueous layer thus obtained, and the resultant mixture was heated to 65° C. to react for 4 hours.

Workup

  1. additionwas added dropwise
  2. customat room temperature
  3. customover one hour
  4. additionAfter dropwise added
  5. temperaturewas then heated to 70° C.
  6. stirringwas stirred continuously for one hour
  7. temperatureto cool to room temperature
  8. stirringthe mixture was stirred for 30 minutes
  9. customthus obtained at 65° C. over one hour period
  10. customthus obtained
  11. customto react for 4 hours

Sources & evidence

ORD record
ord-6fadad8792d14392a60defd7301d6699
Source dataset
uspto-grants-1993_02
Patent number
US05189224

Reaction notes

Loading…