Ethyl Acetate → 4-(4-Bromo-3,5-dimethylphenoxy)-2-methylbutan-2-ol

HRID 576667Notes

Reaction equation

HRID 576667 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][C:14]([OH:17])([CH3:16])[CH3:15])(=O)=O)=CC=1.[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+].C(OCC)(=O)C>CN(C)C=O.O>[Br:18][C:19]1[C:24]([CH3:25])=[CH:23][C:22]([O:26][CH2:12][CH2:13][C:14]([CH3:16])([OH:17])[CH3:15])=[CH:21][C:20]=1[CH3:27]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 819704-Bromo-3,5-dimethylphenolHCID 140012952-Methyl-4-[(4-methylbenzenesulfonyl)oxy]butan-2-ol

Product 1

HCID 679729214-(4-Bromo-3,5-dimethylphenoxy)-2-methylbutan-2-olYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixed solution of 3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate (4.24 g) synthesized in accordance with the method described in [WO 2009/067613 pamphlet, Example 308], 4-bromo-3,5-dimethylphenol (3.0 g), and potassium carbonate (3.09 g) in N,N-dimethylformamide (15 mL) was stirred at 80° C. for 3 hours. To the reaction mixture, ethyl acetate (200 mL) and water (100 mL) were added and the mixture was extracted with ethyl acetate. The organic phase was successively washed with water (50 mL) and brine (50 mL) and then dried over anhydrous sodium sulfate. From the organic phase, the solvent was removed by evaporation under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=80:20 to 70:30). From the eluted solution, the solvent was removed by evaporation under reduced pressure to give the title compound (3.9 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was successively washed with water (50 mL) and brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customFrom the organic phase, the solvent was removed by evaporation under reduced pressure
  5. customthe resultant residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=80:20 to 70:30)
  6. customFrom the eluted solution, the solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-ac5c2ffb162c4fcc90a02d38236125b9
Source dataset
uspto-grants-2015_05
Patent number
US09040525B2

Reaction notes

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