Potassium Carbonate → Ethyl 2-(2-(methylsulfonyl)phenoxy)acetate

HRID 1429463Notes

Reaction equation

HRID 1429463 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])(=[O:4])=[O:3].Br[C:13](C)(C)[C:14]([O:16][CH2:17][CH3:18])=[O:15].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 5989982-Methanesulfonylphenol

Product 1

HCID 86729449Ethyl 2-(2-(methylsulfonyl)phenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(methylsulfonyl)phenol (200 mg, 1.16 mmol) in CH3CN (10 mL) was added ethyl 2-bromo-2-methylpropanoate (232 mg, 1.39 mmol) and K2CO3 (690 mg, 5 mmol) at 25° C. The mixture was refluxed for 16 h and then quenched by addition of water (100 mL). The resulting mixture was extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to give the title compound which was used in next step without further purification.

Workup

  1. temperatureThe mixture was refluxed for 16 h
  2. customquenched by addition of water (100 mL)
  3. extractionThe resulting mixture was extracted with ethyl acetate (2×50 mL)
  4. washThe combined organic layers were washed with brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5134daeec66745a0afe9ccc68c6815cc
Source dataset
uspto-grants-2015_01
Patent number
US08940726B2

Reaction notes

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