Diethyl Ether → Ethyl 2-(2-chlorophenoxy)acetate

HRID 18828

Reaction equation

HRID 18828 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].CCOCC>CN(C=O)C>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[CH3:21]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 72452-ChlorophenolHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 302826Ethyl 2-(2-chlorophenoxy)acetateYield 97.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chlorophenol (2.06 mL, 19.9 mmol) in DMF (40 mL) is added potassium carbonate (3.03 g, 21.9 mmol) and ethyl bromoacetate (2.3 mL, 20.7 mmol), and the mixture is stirred at 80° C. for 18 h. Et2O is added, and the mixture is washed with water, brine, dried (MgSO4), and filtered. The filtrate is evaporated, and the residue is purified by chromatography in silica gel; elution with EtOAc:dichloromethane:hexane (10:5:85) gives 4.17 g of the product 465. 1H NMR (CDCl3) δ 7.38 (d, 1H), 7.21 (t, 1H), 6.92 (t, 1H), 6.84 (d, 1H), 4.70 (s, 2H), 4.27 (q, 2H), 1.29 (t, 3H); MS: m/z 215, 217 (M++1).

Workup

  1. washthe mixture is washed with water, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate is evaporated
  5. customthe residue is purified by chromatography in silica gel
  6. washelution with EtOAc:dichloromethane:hexane (10:5:85)

Sources & evidence

ORD record
ord-b29967885a46478f8ec56bcdaffb4281
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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