Ethyl bromoacetate → Ethyl 2-(3,4-dinitrophenoxy)acetate

HRID 415050Notes

Reaction equation

HRID 415050 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:13])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])([O-:3])=[O:2].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[O:13][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 113483,4-Dinitrophenol

Product 1

HCID 57763328Ethyl 2-(3,4-dinitrophenoxy)acetateYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A round-bottom flask was charged with 3,4-dinitrophenol (11.04 g, 60 mmol, commercially available from Fluka-Sigma-Aldrich), ethyl bromoacetate (11.02 g, 66 mmol), acetonitrile (120 mL) and cesium carbonate (21.6 g). The mixture was stirred at room temperature overnight. The mixture was filtered, and the recovered solid was washed with ethyl acetate. The filtrate was further diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate and combined organic solvent was washed with saturated brine, dried and concentrated under reduced pressure. The residue was triturated with ether to give ethyl 2-(3,4-dinitrophenoxy)acetate (13.0 g, 80% yield). 1H-NMR (400 MHz, MeOH-d4): δ 8.15 (d, 1H), 7.55 (s, 1H), 7.35 (d, 1H), 4.95 (s, 2H), 4.23 (q, 2H), 1.25 (t, 3H). MS (EI): 271 (MH+).

Workup

  1. filtrationThe mixture was filtered
  2. washthe recovered solid was washed with ethyl acetate
  3. additionThe filtrate was further diluted with ethyl acetate and water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwas washed with saturated brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-c6f3b193c5694213beed9195934b8d1d
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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