2-Bromopyridine → 2-(4-Chlorophenyl)pyridine

HRID 1639935Notes

Reaction equation

HRID 1639935 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acid

Product 1

HCID 27578492-(4-Chlorophenyl)pyridineYield 56%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Under a nitrogen stream, 5.0 g (0.032 mol) of 4-chloro-phenyl boronic acid, 10.0 g (0.064 mol) of 2-bromopyridine, 150□ of tetrahydrofuran and 2M potassium carbonate solution (20□) were placed into a 2-neck round flask 250□ and then 0.37 g (3 mol %) of palladium tetrakistriphenylphosphine [(pd(PPh3)4] was added as a catalyst. After the resulting solution was heated to reflux at 80° C. for 24 hours, the reaction was terminated. The resulting mixture was poured into a beaker containing 200□ of distilled water. After extraction with ether (150□) three times, 10 g of magnesium sulfate was added. The resulting solution was stirred by a rotary stirrer for 30 minutes and then the extraction mixture was filtered. After removing the solvent using a rotary evaporator, the residue was subjected to column chromatography using dichloromethane as a developing solvent and then distilled under reduced pressure to give the 2-(4-chloro-phenyl)pyridine. The yield was 56%.

Workup

  1. temperatureAfter the resulting solution was heated
  2. customthe reaction was terminated
  3. additionThe resulting mixture was poured into a beaker
  4. additioncontaining 200□ of distilled water
  5. extractionAfter extraction with ether (150□) three times, 10 g of magnesium sulfate
  6. additionwas added
  7. filtrationthe extraction mixture was filtered
  8. customAfter removing the solvent
  9. customa rotary evaporator
  10. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-2275bb41e98b4909b965c0ae7f57ad1d
Source dataset
uspto-grants-2012_02
Patent number
US08110642B2

Reaction notes

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