Water → Methyl 4-(2-fluoroethoxy)benzoate

HRID 544917Notes

Reaction equation

HRID 544917 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.Br[CH2:13][CH2:14][F:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:15][CH2:14][CH2:13][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromide

Product 1

HCID 10943448Methyl 4-(2-fluoroethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 4-hydroxybenzoate (4.03 g), 1-bromo-2-fluoroethane (5.05 g) and potassium carbonate (10.98 g) in N,N-dimethylformamide (68 ml) was stirred at 70° C. for 1 hour. The reaction mixture was cooled to room temperature, and thereto was added water. The mixture was extracted with ethyl acetate, and the organic layer was washed successively with water and brine, and then dried over magnesium sulfate. The insoluble materials were filtered off, and the filtrate was evaporated under reduced pressure to give methyl 4-(2-fluoroethyloxy)benzoate, which was used in the subsequent step without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed successively with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe insoluble materials were filtered off
  6. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0dc1778103604f459c55a024e9669f9c
Source dataset
uspto-grants-2011_05
Patent number
US07935674B2

Reaction notes

Loading…