Water → HCID 57585897, compound

HRID 547655Notes

Reaction equation

HRID 547655 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+].O>CS(C)=O.FC1C=CC(C=O)=CC=1>[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

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 680234-FluorobenzaldehydeHCID 37588824-Amino-3-Nitrophenol

Product 1

HCID 57585897HCID 57585897, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 680234-FluorobenzaldehydeCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-amino-3-nitrophenol (1.54 g; 10.0 mmol), 4-fluorobenzaldehyde (1.05 mL; 10.0 mmol) and Cs2CO3 (3.91 g; 12.0 mmol) in anhydrous dimethylsulfoxide (10 mL) was heated at 80 degrees Centigrade, under nitrogen. An additional portion of 4-fluorobenzaldehyde (0.050 mL; 0.50 mmol) was added after 1 hour and heating was continued. After 2 hours the mixture was cooled, poured into water and extracted three times with ethyl acetate. Combined organics were washed (H2O, brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (ethyl acetate/hexanes), affording 2.56 g of 4-[(4-Amino-3-nitrophenyl)oxy]benzaldehyde as an orange solid. 1H NMR (400 MHz, CDCl3) delta ppm 6.11 (br. s, 2H), 6.90 (d, J=9.1 Hz, 1H), 7.04 (m, 2H), 7.20 (dd, J=9.0, 2.8 Hz, 1H), 7.86 (m, 2H), 7.89 (d, J=2.7 Hz, 1H), 9.93 (s, 1H) ppm. (M+H) 259, 2.33 min (LC/MS method A).

Workup

  1. temperaturewas heated at 80 degrees Centigrade, under nitrogen
  2. temperatureheating
  3. temperatureAfter 2 hours the mixture was cooled
  4. extractionextracted three times with ethyl acetate
  5. washCombined organics were washed (H2O, brine)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-45a4cf8150a04638aa3dc73993b065ba
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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