4-Nitrophenol → HCID 2942627, compound

HRID 2086142Notes

Reaction equation

HRID 2086142 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)([O-:9])=[O:8].[CH2:17]([O:19][C:20](=[O:29])[CH:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)Br)[CH3:18]>CN(C=O)C>[CH2:17]([O:19][C:20](=[O:29])[CH:21]([O:16][C:13]1[CH:14]=[CH:15][C:10]([N+:7]([O-:9])=[O:8])=[CH:11][CH:12]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:18]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10796Cesium carbonateHCID 97780Ethyl bromophenylacetate

Product 1

HCID 2942627HCID 2942627, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of cesium carbonate (2.51 g, 7.70 mmol) in DMF (30 mL) was added 4-nitrophenol(1.07 g, 7.70 mmol). After stirring at room temperature under argon for 30 minutes, ethyl-alpha-bromophenylacetate (1.70 g, 7.00 mmol) was added to the suspension and the resulting mixture was stirred at room temperature overnight. The reaction was then quenched with water and extracted with EtOAc. The organic extracts were washed with water, brine, and dried over Na2SO4. After removing the solvent under reduced pressure, the crude product was used in the next reaction without further purification. 1H NMR (400 MHz, CDC3) δ8.20 (d, 2H) 7.60-7.37 (m, 5H), 7.05 (d, 2H), 5.70 (s, 1H), 4.20 (m, 2H), 1.22 (t, 3H). MH+ 303.

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe reaction was then quenched with water
  3. extractionextracted with EtOAc
  4. washThe organic extracts were washed with water, brine
  5. dry with materialdried over Na2SO4
  6. customAfter removing the solvent under reduced pressure
  7. customthe crude product was used in the next reaction without further purification

Sources & evidence

ORD record
ord-cc8230505f1b464ebb8bd850d13fa868
Source dataset
uspto-grants-2004_04
Patent number
US06723749B2

Reaction notes

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