Potassium Phosphate, Tribasic → 2-Nitro-6-cyclopropylbenzonitrile

HRID 631879Notes

Reaction equation

HRID 631879 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[C:4]#[N:5].[CH:13]1(B(O)O)[CH2:15][CH2:14]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N+:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([CH:13]2[CH2:15][CH2:14]2)[C:3]=1[C:4]#[N:5])([O-:12])=[O:11]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 249719882-Bromo-6-nitrobenzonitrile

Product 1

HCID 682964052-Nitro-6-cyclopropylbenzonitrileYield 109.9%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

2-Bromo-6-nitrobenzonitrile (0.56 g), cyclopropyl boronic acid (0.63 g), palladium (II) acetate (0.055 g), tricyclohexylphosphine (0.135 g) and potassium phosphate tribasic (2.36 g) were dissolved in a mixture of toluene (15 mL) and water (3 mL). The mixture was heated at 100° C. under nitrogen for 18 hours. The mixture was cooled and then partitioned between water and DCM. The organic solution was separated, dried with magnesium sulfate, filtered and the solvent was removed under vacuum. The residue was purified by flash chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane. The fractions containing the desired product were combined and evaporated to give the title compound as a light yellow solid (0.51 g).

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between water and DCM
  3. customThe organic solution was separated
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed under vacuum
  7. customThe residue was purified by flash chromatography on silica
  8. washeluting with a mixture of ethyl acetate and cyclohexane
  9. additionThe fractions containing the desired product
  10. customevaporated

Sources & evidence

ORD record
ord-1b1d10b94dab494992f606472c1216e2
Source dataset
uspto-grants-2016_04
Patent number
US09321740B2

Reaction notes

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