4-Fluorophenol → Tert-butyl 2-(4-fluorophenoxy)acetate

HRID 1895920Notes

Reaction equation

HRID 1895920 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7]Br)([CH3:4])([CH3:3])[CH3:2].[F:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.[OH-].[Na+]>CN(C)C=O>[F:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:9])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetate

Product 1

HCID 67118384Tert-butyl 2-(4-fluorophenoxy)acetateYield 95.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl-2-bromoacetate (1.95 g, 10.0 mmol) was added to a mixture of 4-fluorophenol (1.12 g, 10.0 mmol) and NaOH (400 mg, 10.0 mmol) in N,N-dimethylformamide (15 ml) and stirred at room temperature for 17 hours. The reaction was quenched with H2O (50 ml) and extracted by ethyl acetate (50 ml×3). The combined organic phase was washed with H2O (50 ml×4) and brine (50 ml), dried over Na2SO4, filtered and concentrated in vacuo to give tert-butyl 2-(4-fluorophenoxy)acetate (2.16 g, 95%) as yellow oil: LC-MS: 171 [M−55]+.

Workup

  1. customThe reaction was quenched with H2O (50 ml)
  2. extractionextracted by ethyl acetate (50 ml×3)
  3. washThe combined organic phase was washed with H2O (50 ml×4) and brine (50 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-41f6f57ca2144bdc9203b299732a0e85
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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