Water → ethyl 2-(4-fluorophenoxy)-2-methylpropanoate

HRID 389081Notes

Reaction equation

HRID 389081 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester

Product 1

HCID 1531585ethyl 2-(4-fluorophenoxy)-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-fluorophenol (5.0 g) was dissolved in DMF (50 ml), ethyl 2-bromo-2-methylpropanoate (13.3 ml) and potassium carbonate (9.25 g) were added thereto, followed by stirring at 100° C. for 2 hours. The reaction solution was cooled to room temperature and water was added thereto, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=19:1) to obtain ethyl 2-(4-fluorophenoxy)-2-methylpropanoate (5.13 g) as a colorless oily product.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=19:1)

Sources & evidence

ORD record
ord-7631b3d62b9744f99570449c10a72649
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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