3-Hydroxybenzaldehyde → 3-(4-Chloro-2-nitro-phenoxy)-benzaldehyde

HRID 2358757Notes

Reaction equation

HRID 2358757 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[OH:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[CH:16]=[O:17])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 27949042-Bromo-5-chloronitrobenzene

Product 1

HCID 92813413-(4-Chloro-2-nitro-phenoxy)-benzaldehydeYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of DMF (50 mL) was added 1-bromo-2-nitro-4-chloro-benzene (10.0 g, 42.2 mmol), 3-hydroxybenzaldehyde (5.2 g, 42.2 mmol), and K2CO3 (11.5 g, 84.6 mmol). The solution was heated to 85° C. and stirred overnight. The reaction was poured into distill water and extracted with ethyl acetate. The combined organic layers were washed with distilled water, brine, and dried over Na2SO4, filtered and concentrated under vacuum giving the crude title compound. This solid was purified by silica gel column chromatography eluting with hexanes/ethyl acetate (4:1) to give the title compound (4.4 gm, 41%).

Workup

  1. additionThe reaction was poured
  2. distillationinto distill water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with distilled water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customgiving the crude title compound
  9. customThis solid was purified by silica gel column chromatography
  10. washeluting with hexanes/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-945b1e6ae39a4faea15462eb64128afc
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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