Ethyl bromoacetate → Ethyl 2-(4-fluorophenoxy)acetate

HRID 1511879Notes

Reaction equation

HRID 1511879 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 97324-FluorophenolHCID 24758Sodium hydride

Product 1

HCID 4476170Ethyl 2-(4-fluorophenoxy)acetateYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4-fluorophenol (2.00 g, 17.84 mmol) in DMF (10 mL) was added dropwise to a stirred suspension of NaH in DMF (2.0 mL) at around 10° C. Ethyl bromoacetate (2.483 mL, 22.30 mmol) was added dropwise and then the reaction mixture was allowed to warm up to room temperature for 4 hours. The solvent was removed under vacuum and the residue was dissolved in methylene chloride and washed 2 times with water, dried over MgSO4, filtered and concentrated to dryness. The crude product was purified on silica gel using (4:1 heptane:EtOAc as eluent) to give ethyl 2-(4-fluorophenoxy)acetate (3.12 g, 95%).

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washwashed 2 times with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe crude product was purified on silica gel using (4:1 heptane:EtOAc as eluent)

Sources & evidence

ORD record
ord-a83c8aa3f0e741628ae2107fc33c19d9
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

Loading…