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

HRID 1626948Notes

Reaction equation

HRID 1626948 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.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=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 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (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). The mixture was sparged with nitrogen for 10 min whereupon 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 and progress monitored by TLC. After heating for 6 h the reaction was then cooled to RT and diluted with EtOAc (100 mL). The organic layer was separated and concentrated in vacuo. Purification of the residue by column chromatography on silica gel to gave (iv) (2 g, 78%).

Workup

  1. additionwere added
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux
  4. temperatureAfter heating for 6 h the reaction
  5. customThe organic layer was separated
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-aa824f464fc74c548a152ee1ff54cb09
Source dataset
uspto-grants-2014_07
Patent number
US08785478B2

Reaction notes

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