Potassium Carbonate → HCID 67813216, compound

HRID 593201Notes

Reaction equation

HRID 593201 reaction equation
Br[CH2:2][C:3](=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5].[F:9][C:10]([F:20])([F:19])[O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:5][C:4]([CH3:7])([CH3:6])[C:3](=[O:8])[CH2:2][O:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:10]([F:9])([F:19])[F:20])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21642BromopinacoloneHCID 70015p-(Trifluoromethoxy)phenol

Product 1

HCID 67813216HCID 67813216, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

With stirring and at room temperature, a solution of 5.5 g (31 mmol) of 1-bromo-3,3-dimethylbutan-2-one in 50 ml of acetonitrile was slowly added dropwise to a mixture of 5.5 g (31 mmol) of 4-trifluoromethoxyphenol and 4.27 g (31 mmol) of potassium carbonate in 100 ml of acetonitrile. After the addition had ended, the reaction mixture was stirred at reflux temperature overnight. The solid was filtered off and the filtrate was concentrated. The residue was taken up in 50 ml of ethyl acetate and the organic phase was washed with ice-cold 1M aqueous sodium hydroxide solution and water. The organic phase was separated off, dried over sodium sulphate, filtered and concentrated. The crude product was then purified by column chromatography. This gave 2.22 g (26%) of the desired product.

Workup

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred
  3. temperatureat reflux temperature overnight
  4. filtrationThe solid was filtered off
  5. concentrationthe filtrate was concentrated
  6. washthe organic phase was washed with ice-cold 1M aqueous sodium hydroxide solution and water
  7. customThe organic phase was separated off
  8. dry with materialdried over sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was then purified by column chromatography

Sources & evidence

ORD record
ord-92f3e620d6094e0f9a3ce83e6662536d
Source dataset
uspto-grants-2016_01
Patent number
US09241487B2

Reaction notes

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