Ethyl bromoacetate → Ethyl 2-(4-nitrophenoxy)acetate

HRID 71334

Reaction equation

HRID 71334 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C([O-])([O-])=[O:12].[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CC(C)=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:12][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 111373-NitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 308938Ethyl 2-(4-nitrophenoxy)acetateYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A dry reaction flask equipped with a reflux condenser, N2 inlet and a magnetic stirring bar was charged with 3-nitrophenol (76.45 g, 550 mmol), K2CO3 (76.45 g, 550 mmol) and dry acetone (500 mL) under N2 atmosphere. To this at room temperature was added ethyl bromoacetate (55.44 mL, 500 mmol) over a period of 15 min. The reaction mixture was refluxed for 16 h, cooled and poured over ice-water (4 Kg). The resulting aqueous solution was extracted with CH2Cl2 (3×500 mL), dried over anhydrous Na2SO4 and solvent was removed to obtain 103 g (92%) of the desired ethyl 4-nitrophenoxyacetate. 1H NMR (CDCl3): δ 8.20 (d, 2H, J=8.2 Hz), 6.95 (d, 2H, J=8.1 Hz), 4.72 (s, 2H), 4.25 (q, 2H), 1.23 (t, 3H); LCMS: ret. time: 27.07 min.; purity: 100%; MS: 267 (M+acetonitrile).

Workup

  1. customA dry reaction flask
  2. customequipped with a reflux condenser, N2 inlet and a magnetic stirring bar
  3. temperatureThe reaction mixture was refluxed for 16 h
  4. temperaturecooled
  5. extractionThe resulting aqueous solution was extracted with CH2Cl2 (3×500 mL)
  6. dry with materialdried over anhydrous Na2SO4 and solvent
  7. customwas removed

Sources & evidence

ORD record
ord-4eb61bebf99d4a4e982f90071ee3170f
Source dataset
uspto-grants-2014_09
Patent number
US08822685B2

Linked notes

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