4-Hydroxybenzaldehyde → 4-[(5-Amino-2-fluoro-4-nitrophenyl)oxy]benzaldehyde

HRID 547652Notes

Reaction equation

HRID 547652 reaction equation
Cl[C:2]1[C:3]([F:12])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].CC(C)([O-])C.[K+].[OH:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1.O>CN(C)C=O>[NH2:7][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]([F:12])=[C:2]([O:19][C:20]2[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 5178355-Chloro-4-fluoro-2-nitroanilineHCID 23665647Potassium tert-butoxide

Product 1

HCID 575858884-[(5-Amino-2-fluoro-4-nitrophenyl)oxy]benzaldehydeYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-chloro-4-fluoro-2-nitroaniline (0.380 g, 1.99 mmol), potassium t-butoxide (0.269 g, 2.39 mmol), and 4-hydroxybenzaldehyde (0.292 g, 2.39 mmol) in dimethylformamide (5 mL) was heated to 80 degrees Centigrade for 6 hours and then cooled. Water was added and the organics extracted using ethyl acetate (2×50 mL). The combined organics were then washed one time in brine and then dried (Na2SO4), filtered and concentrated. Chromatography on silica gel using a gradient of 20%-30% ethyl acetate/hexanes eluted the product to give 0.468 g of 4-[(5-amino-2-fluoro-4-nitrophenyl)oxy]benzaldehyde as an orange solid.

Workup

  1. temperaturecooled
  2. extractionthe organics extracted
  3. washThe combined organics were then washed one time in brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washChromatography on silica gel using a gradient of 20%-30% ethyl acetate/hexanes eluted the product

Sources & evidence

ORD record
ord-8e7c3b12967e445d9615919a361f1b13
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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