Cesium carbonate → HCID 23110280, compound

HRID 2356944Notes

Reaction equation

HRID 2356944 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].Br[CH2:14][CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18].C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[Na+]>CN(C)C=O>[CH2:17]([O:16][CH:15]([O:19][CH2:20][CH3:21])[CH2:14][O:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH3:18]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 694712-Methoxy-5-nitrophenolHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 23110280HCID 23110280, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 7.50 g 2-methoxy-5-nitro-phenol, 9.61 g 2-bromo-1,1-diethoxy-ethane and 15.89 g cesium carbonate in 75 ml N,N-dimethylformamide was stirred at 100° C. for 4 hours. After cooling to room temperature the reaction mixture was treated with an aqueous 1% solution of sodium hydroxide and extracted twice with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. After filtration and concentration of the solvent under reduced pressure the residue was dissolved in a mixture of ethyl acetate and n-heptane. After removal of the ethyl acetate under reduced pressure the resulting residue was filtered off and the clear solution concentrated under reduced pressure. The residue was directly subjected to the subsequent reaction without further purification. Yield: 9.45 g

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationAfter filtration and concentration of the solvent under reduced pressure the residue
  5. dissolutionwas dissolved in a mixture of ethyl acetate and n-heptane
  6. customAfter removal of the ethyl acetate under reduced pressure the resulting residue
  7. filtrationwas filtered off
  8. concentrationthe clear solution concentrated under reduced pressure
  9. customThe residue was directly subjected to the subsequent reaction without further purification

Sources & evidence

ORD record
ord-22f040f69de640ab88cb0522b3d75a0f
Source dataset
uspto-grants-2010_07
Patent number
US07759379B2

Reaction notes

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