4-Hydroxybenzaldehyde → 4-{[5-Amino-4-nitro-2-(trifluoromethyl)phenyl]oxy}benzaldehyde

HRID 547651Notes

Reaction equation

HRID 547651 reaction equation
Cl[C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].CC(C)([O-])C.[K+].[OH:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1.O>CN(C)C=O>[NH2:7][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]([C:12]([F:15])([F:14])[F:13])=[C:2]([O:22][C:23]2[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 27738135-Chloro-2-nitro-4-(trifluoromethyl)anilineHCID 23665647Potassium tert-butoxide

Product 1

HCID 575859334-{[5-Amino-4-nitro-2-(trifluoromethyl)phenyl]oxy}benzaldehydeYield 74.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-chloro-2-nitro-4-(trifluoromethyl)aniline (0.240 g, 1.00 mmol), potassium t-butoxide (0.135 g, 1.2 mmol), and 4-hydroxybenzaldehyde (0.147 g, 1.2 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 once in brine and then dried (Na2SO4), filtered and concentrated. Chromatography on silica gel using a gradient of 30%-40% ethyl acetate/hexanes eluted the product to give 0.243 g of 4-{[5-amino-4-nitro-2-(trifluoromethyl)phenyl]oxy}benzaldehyde as an yellowish solid.

Workup

  1. temperaturecooled
  2. extractionthe organics extracted
  3. washThe combined organics were then washed once in brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washChromatography on silica gel using a gradient of 30%-40% ethyl acetate/hexanes eluted the product

Sources & evidence

ORD record
ord-b63e4eca6433434f96ccedff54070bd2
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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