Potassium Carbonate → 1-Cyclopropyl-4-nitrobenzene

HRID 1898332

Reaction equation

HRID 1898332 reaction equation
[CH:1]1(B(O)O)[CH2:3][CH2:2]1.Br[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH:1]1([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 114661-Bromo-4-nitrobenzeneHCID 2760897Cyclopropylboronic acid

Product 1

HCID 3127131-Cyclopropyl-4-nitrobenzeneYield 92,855.398%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of cyclopropyl boronic acid (0.637 g, 0.00742 mmol) in dry toluene, were added 4-bromo nitrobenzene (1.00 g, 0.00495 mmol) and tetrakis triphenylphosphine palladium (0.099 g, 0.0099 mol). Degassed the reaction mixture for 30 minutes then added potassium carbonate (1.36 g, 0.009 mmol). The reaction mass was refluxed for 48 h. The excess of solvent was removed under vacuum and the reaction mass was diluted with water and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated. The obtained crude was purified by column chromatography on silica gel eluting with 4% DCM: MeOH to afford 0.750 g of the desired product. 1HNMR (DMSO-d6): δ 0.82-0.84 (m, 2H), 1.09-1.13 (m, 2H), 2.01 (m, 1H), 7.32 (d, J=8.7 Hz, 2H), 8.09 (d, J=8.7 Hz, 2H).

Workup

  1. customDegassed the reaction mixture for 30 minutes
  2. temperatureThe reaction mass was refluxed for 48 h
  3. customThe excess of solvent was removed under vacuum
  4. additionthe reaction mass was diluted with water
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous sodium sulphate
  8. concentrationconcentrated
  9. customThe obtained crude
  10. customwas purified by column chromatography on silica gel eluting with 4% DCM

Sources & evidence

ORD record
ord-a321db58508d46919714678f2ca072d6
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Linked notes

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