Ethyl bromoacetate → Ethyl (3-cyanophenoxy)acetate

HRID 606460Notes

Reaction equation

HRID 606460 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C(=O)([O-])[O-].[K+].[K+].[OH:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[C:18]#[N:19]>C1COCC1>[C:18]([C:17]1[CH:16]=[C:15]([O:14][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:22]=[CH:21][CH:20]=1)#[N:19]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 133943-Cyanophenol

Product 1

HCID 24696095Ethyl (3-cyanophenoxy)acetateYield 101.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl bromoacetate (14.7 g, 88.1 mmol) was added dropwise to a suspension of potassium carbonate (12.8 g, 92.3 mmol) and 3-hydroxybenzonitrile (10.0 g, 83.9 mmol) in THF (50 mL) at room temperature, and the mixture was stirred at 50° C. for 24 hr. The mixture was extracted with ethyl acetate and saturated aqueous ammonium chloride solution, and the organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated to give the title compound as a pale-yellow powder (17.5 g, 99%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate and saturated aqueous ammonium chloride solution
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-41c53868d8584131b7fa8886f4ef2b4c
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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