Potassium Carbonate → 4-(4-Bromo-3,5-dimethylphenoxy)-2-methylbutan-2-ol

HRID 2170923Notes

Reaction equation

HRID 2170923 reaction equation
[OH:1][C:2]([CH3:17])([CH3:16])[CH2:3][CH2:4]OS(C1C=CC(C)=CC=1)(=O)=O.[Br:18][C:19]1[C:24]([CH3:25])=[CH:23][C:22]([OH:26])=[CH:21][C:20]=1[CH3:27].C(=O)([O-])[O-].[K+].[K+].[NH4+].[Cl-]>CN(C=O)C>[Br:18][C:19]1[C:24]([CH3:25])=[CH:23][C:22]([O:26][CH2:4][CH2:3][C:2]([CH3:17])([OH:1])[CH3:16])=[CH:21][C:20]=1[CH3:27]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 819704-Bromo-3,5-dimethylphenolHCID 140012952-Methyl-4-[(4-methylbenzenesulfonyl)oxy]butan-2-ol2×

Product 1

HCID 679729214-(4-Bromo-3,5-dimethylphenoxy)-2-methylbutan-2-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

40.7 g (157 mmol) of toluene-4-sulfonic acid 3-hydroxy-3-methylbutyl ester (product of step 1), 34.0 g (169 mmol) of 4-bromo-3,5-dimethylphenol and 25.0 g (180 mmol) of potassium carbonate are dissolved in 114 ml DMF. The reaction mixture is stirred at 50° C. for 16 h. The reaction mixture is poured into aq. NH4Cl solution and stirred. Then the layers are separated. The aq. layer is extracted with DCM. The combined organic layers are washed with water and dried. The solvent is evaporated and the residue is chromatographed on silica gel (PE/EtOAc) to give the title compound. Yield: 38.3 g; Mass spectrum (ESI+): m/z=287 [M+H]+.

Workup

  1. stirringstirred
  2. customThen the layers are separated
  3. extractionThe aq. layer is extracted with DCM
  4. washThe combined organic layers are washed with water
  5. customdried
  6. customThe solvent is evaporated
  7. customthe residue is chromatographed on silica gel (PE/EtOAc)

Sources & evidence

ORD record
ord-a9989e92bfbc4f578e17c6e70b922475
Source dataset
uspto-grants-2015_06
Patent number
US09051289B2

Reaction notes

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