Cesium carbonate → HCID 57585897, compound

HRID 547622Notes

Reaction equation

HRID 547622 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].F[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680234-FluorobenzaldehydeHCID 37588824-Amino-3-Nitrophenol

Product 1

HCID 57585897HCID 57585897, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-amino-3-nitrophenol (25 g, 162 mmol), 4-fluorobenzaldehyde (19.1 g, 154 mmol) and cesium carbonate (58 g, 178 mmol) were stirred in dimethylformamide at 85 degrees centigrade for 20 minutes and then 45 degrees Centigrade for approximately 18 hours. The reaction was allowed to cool to room temperature then filtered through celite and eluted with ethyl acetate. Water, brine and ethyl acetate were added to the filtrate which was then filtered through a glass wool packed Alltech 75 mL Extract-Clean™ filter column. The filtrate was separated into two portions and each was extracted with ethyl acetate then washed with brine four times. The organic layers were combined, dried over magnesium sulfate, concentrated onto basic alumina and purified by silica gel column chromatography (0 to 100% ethyl acetate in hexanes to give 23 g of 4-[(4-amino-3-nitrophenyl)oxy]benzaldehyde. (M+1) 259.0, 2.39 min (LC/MS method A)

Workup

  1. filtrationthen filtered through celite
  2. washeluted with ethyl acetate
  3. additionWater, brine and ethyl acetate were added to the filtrate which
  4. filtrationwas then filtered through a glass wool
  5. filtrationfilter column
  6. customThe filtrate was separated into two portions
  7. extractioneach was extracted with ethyl acetate
  8. washthen washed with brine four times
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated onto basic alumina
  11. custompurified by silica gel column chromatography (0 to 100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d07135df0b0d45ba800cb1e3ce9aa6b1
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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