Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 4-Bromo-2-chloro-1-(2-chloroethoxy)benzene

HRID 1773969Notes

Reaction equation

HRID 1773969 reaction equation
C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S(O[CH2:17][CH2:18][Cl:19])(=O)=O)=CC=1.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([Cl:29])[CH:23]=1>CN(C=O)C>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:17][CH2:18][Cl:19])=[C:24]([Cl:29])[CH:23]=1

Participants

5

Reactant 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 11430Potassium CarbonateHCID 198594-Bromo-2-chlorophenol

Product 1

HCID 431356234-Bromo-2-chloro-1-(2-chloroethoxy)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (8.29 g, 60 mmol, 3.0 eq.) and 2-chloroethyl p-toluenesulfonate (5.16 g, 22 mmol, 1.1 eq.) were added in sequence to a solution of 4-bromo-2-chlorophenol (4.19 g, 20 mmol, 1.0 eq.) in DMF (25 mL). The resulting mixture was heated up to 60° C. and stirred at that temperature for 4 hours. The mixture was allowed to cool down to r.t. and was partitioned between AcOEt (290 mL) and water (120 mL). The layers were separated. The org. phase was washed with water (4×120 mL), dried over MgSO4, filtered, and concentrated in vacuo to give 4-bromo-2-chloro-1-(2-chloro-ethoxy)-benzene as a colorless oil that solidified upon standing. The product was used without further purification.

Workup

  1. temperatureto cool down to r.t.
  2. customwas partitioned between AcOEt (290 mL) and water (120 mL)
  3. customThe layers were separated
  4. washphase was washed with water (4×120 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e97a8e7e3c734083a67b37c694b84edd
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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