4-Hydroxybenzaldehyde → HCID 57585976, compound

HRID 547647Notes

Reaction equation

HRID 547647 reaction equation
[F:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:6]=[C:7](F)[CH:8]=1)[NH2:5].C([O-])([O-])=O.[Cs+].[Cs+].[OH:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1.O>CS(C)=O>[NH2:5][C:4]1[CH:6]=[C:7]([O:19][C:20]2[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=2)[CH:8]=[C:2]([F:1])[C:3]=1[N+:10]([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 10796Cesium carbonateHCID 2230923,5-difluoro-2-nitroaniline

Product 1

HCID 57585976HCID 57585976, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 3,5-difluoro-2-nitroaniline (0.400 g, 2.30 mmol), Cs2CO3 (1.87 g, 5.74 mmol), and 4-hydroxybenzaldehyde (0.309 g, 2.53 mmol) in dimethylsulfoxide (5 mL) was heated at 80 degrees Centigrade for 2 hours and then cooled. Water was added and the organics extracted using ethyl acetate (2×50 mL). The combined organics were washed once in brine and dried (Na2SO4), filtered and concentrated. Chromatography on silica gel using a gradient of 20%-60% ethyl acetate/hexanes eluted the product to give 0.536 g of 4-[(3-amino-5-fluoro-4-nitrophenyl)oxy]benzaldehyde as a yellow solid.

Workup

  1. temperaturecooled
  2. extractionthe organics extracted
  3. washThe combined organics were washed once in brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washChromatography on silica gel using a gradient of 20%-60% ethyl acetate/hexanes eluted the product

Sources & evidence

ORD record
ord-6f81b5c1630642d38daa6b4d042c505e
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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