Potassium Carbonate → 3-(3-Chlorophenyl)pyridine

HRID 1639943Notes

Reaction equation

HRID 1639943 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Br[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH: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:3]=[C:4]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 142684-BromopyridineHCID 2734323(3-Chlorophenyl)boronic acid

Product 1

HCID 149214653-(3-Chlorophenyl)pyridineYield 50%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

This Example was carried out in the same manner as Example 1, except that 5.0 g (0.032 mol) of 3-chloro-phenyl boronic acid, 10.0 g (0.064 mol) of 4-bromopyridine, 150□ of tetrahydrofuran and 2M potassium carbonate solution (20□) were added and then 0.37 g (3 mol %) of palladium tetrakistriphenylphosphine [(pd(PPh3)4] was used as a catalyst. Finally, after the resulting solution was heated to reflux at 80° C. for 24 hours, the 3-(3-chloro-phenyl)pyridine was isolated. The yield was 50%.

Workup

  1. additionwere added
  2. temperatureFinally, after the resulting solution was heated

Sources & evidence

ORD record
ord-ab1eecb6e3bb41be9e3b4dacf9d7f9a9
Source dataset
uspto-grants-2012_02
Patent number
US08110642B2

Reaction notes

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