Potassium Carbonate → 2-(4-chlorophenyl)-5-nitropyridine

HRID 881758Notes

Reaction equation

HRID 881758 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>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.O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 742994-Chlorophenylboronic acidHCID 782402-Bromo-5-nitropyridine

Product 1

HCID 27638652-(4-chlorophenyl)-5-nitropyridineYield 103.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A flask was charged with 2-bromo-5-nitropyridine (4 g, 19.71 mmol), 4-chlorophenylboronic acid (4.54 g, 27.6 mmol), Pd(PPh3)4 (1.139 g, 0.985 mmol), potassium carbonate (8.16 g, 59.1 mmol), dioxane (40 ml) and water (20 ml) at room temperature. The flask was sealed, flushed with nitrogen for three times and heated at 100° C. for 3 hours. The reaction mixture was diluted with EtOAc (100 ml) and filtered. The filtrate was concentrated. The residue was washed with water by filtration. The afforded solid was dissolved in EtOAc (200 ml) and washed with saturated aqueous sodium bicarbonate solution and brine, dried over Na2SO4, concentrated, and dried under vacuum to afford crude 2-(4-chlorophenyl)-5-nitropyridine (4.8 g, 75% purity, 78% yield) as yellow solid. 1H NMR (400 MHz, DMSO-d6) ppm 7.27-7.36 (m, 4H) 7.51-7.61 (m, 3H).

Workup

  1. customThe flask was sealed
  2. customflushed with nitrogen for three times
  3. additionThe reaction mixture was diluted with EtOAc (100 ml)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. washThe residue was washed with water by filtration
  7. dissolutionThe afforded solid was dissolved in EtOAc (200 ml)
  8. washwashed with saturated aqueous sodium bicarbonate solution and brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated
  11. customdried under vacuum

Sources & evidence

ORD record
ord-f462997f79f64c07b3aa1a5a22c5e1d5
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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