Ethyl bromoacetate → Ethyl 2-(3-nitrophenoxy)acetate

HRID 450052Notes

Reaction equation

HRID 450052 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4].Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>CN(C=O)C>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][O:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=1)[CH3:19]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 111373-NitrophenolHCID 14798Sodium Hydroxide

Product 1

HCID 2741030Ethyl 2-(3-nitrophenoxy)acetateYield 68.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Powdered sodium hydroxide (1 g, 28.77 mmol) was added to a solution of 3-nitro phenol (2 g, 14.35 mmol) in DMF (15 ml) and cooled in an ice-bath. Ethyl bromoacetate (3.2 ml, 28.77 mmol) was added, and the reaction mixture was heated at 90° C. for 7 hr. The reaction mixture was cooled and quenched with ice water. The product was extracted with ethyl acetate, washed with water and dried. Concentration under reduced pressure gave (3-nitrophenoxy)-acetic acid ethyl ester (2.2 g, 68%) as oil.

Workup

  1. temperaturecooled in an ice-bath
  2. temperatureThe reaction mixture was cooled
  3. customquenched with ice water
  4. extractionThe product was extracted with ethyl acetate
  5. washwashed with water
  6. customdried
  7. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-2250c442d6024535bda323607eaefd13
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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