Water → HCID 68562751, compound

HRID 19799Notes

Reaction equation

HRID 19799 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:12])=[C:6]([C:8](O)([CH3:10])[CH3:9])[CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1.CCOCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:12])=[C:6]([C:8]([CH3:10])=[CH2:9])[CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 685596932-(5-Bromo-2-chlorophenyl)propan-2-ol

Product 1

HCID 68562751HCID 68562751, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-(5-bromo-2-chlorophenyl)-propan-2-ol (500 mg, 2 mmol, 1 eq) in toluene (5 ml) was added a catalytic amount of p-toluenesulfonic acid (38 mg, 0.2 mmol, 0.1 eq) and the solution was refluxed under a Dean-Stark H2O separator overnight. The reaction mixture was allowed to cool to RT and was diluted with ether. The mixture was washed with sat. NaHCO3-solution and brine, dried (MgSO4), filtered and concentrated in vacuo to give the desired product (357 mg, 77%) as a colorless oil which did not require further purification.

Workup

  1. washThe mixture was washed with sat. NaHCO3-solution and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a360614174e4bb88cfe428790319bd5
Source dataset
uspto-grants-2010_06
Patent number
US07745477B2

Reaction notes

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