Ethyl bromoacetate → Ethyl 2-(2-(methylsulfonyl)phenoxy)acetate

HRID 1507033Notes

Reaction equation

HRID 1507033 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].C([O-])([O-])=O.[K+].[K+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CC#N.O>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])(=[O:3])=[O:4]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 5989982-Methanesulfonylphenol

Product 1

HCID 86729449Ethyl 2-(2-(methylsulfonyl)phenoxy)acetateYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(methylsulfonyl)phenol (100 mg, 0.58 mmol) and K2CO3 (276 mg, 2 mmol) in CH3CN (10 mL) was added ethyl 2-bromoacetate (115.2 mg, 0.69 mmol) at 25° C. The mixture was heated at 80° C. for 4 h, diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. The crude product was used in the next step without further purification. (140 mg, yield 94%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-8f4369eea7ee4feda7a9a58b0b1562f3
Source dataset
uspto-grants-2015_12
Patent number
US09221794B2

Reaction notes

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