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

HRID 1417992Notes

Reaction equation

HRID 1417992 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 7748Ethyl bromoacetateHCID 111373-NitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 2741030Ethyl 2-(3-nitrophenoxy)acetateYield 98%

Procedure

A mixture of 3-nitrophenol (6.95 g), ethyl bromoacetate (8.35 g) and potassium carbonate (6.9 g) in dry NHP (50 ml) was stirred at room temperature for 48 hours. The reaction mixture was partitioned between water (300 ml) and diethyl ether (75 ml). The organic layer was separated, washed with water, brine and dried (MgSO4). The residue was filtered through silica and eluted with a 3:2 mixture of hexane and ethyl acetate to give ethyl 3-nitrophenoxyacetate as a viscous oil in 98% yield;

Workup

  1. customThe reaction mixture was partitioned between water (300 ml) and diethyl ether (75 ml)
  2. customThe organic layer was separated
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationThe residue was filtered through silica
  6. washeluted with a 3:2 mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-282872132ca042d9b5863032a1a379f1
Source dataset
uspto-grants-1999_03
Patent number
US05880130

Reaction notes

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