Sodium Carbonate → 5-Cyclopropyl-2,4-dinitrobenzaldehyde

HRID 1037521Notes

Reaction equation

HRID 1037521 reaction equation
Br[C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].C(=O)([O-])[O-].[Na+].[Na+].[CH:22]1(B(O)O)[CH2:24][CH2:23]1>C1(C)C=CC=CC=1.O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:22]1([C:2]2[C:3]([N+:13]([O-:15])=[O:14])=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=2)[CH:7]=[O:8])[CH2:24][CH2:23]1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 772315365-Bromo-2,4-dinitrobenzaldehyde

Product 1

HCID 866664205-Cyclopropyl-2,4-dinitrobenzaldehydeYield 78%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of compound (iii) (3 g, 10.9 mmol) in toluene (75 mL) was added a solution of sodium carbonate (2.29 g, 21.8 mmol) in water (15 mL) and the mixture was purged with nitrogen for 10 min. Cyclopropyl boronic acid (1.4 g, 16.4 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.25 g, 0.22 mmol) were added and the reaction mixture was heated at reflux for 6 h (monitored by TLC). The reaction was then cooled to RT and diluted with EtOAc. The aqueous and organic layers were separated. Concentration of the solvent gave the crude product which was purified by column chromatography to give 5-cyclopropyl-2,4-dinitrobenzaldehyde (iv) (2 g, 78%).

Workup

  1. customthe mixture was purged with nitrogen for 10 min
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 6 h (monitored by TLC)
  4. customThe aqueous and organic layers were separated
  5. customConcentration of the solvent gave the crude product which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-1057707b5c004bce8b44dbed437cc971
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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