Potassium Phosphate, Tribasic → 4-(4-Trifluoromethylphenyl)pyridine

HRID 1405446Notes

Reaction equation

HRID 1405446 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[N:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([C:15]2[CH:16]=[CH:17][N:12]=[CH:13][CH:14]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 75806TricyclohexylphosphineHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 6139654-(4-Trifluoromethylphenyl)pyridineYield 121.1%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 1-bromo-4-(trifluoromethyl)benzene (1.0 g, 4.44 mmol, 1.00 equiv), pyridin-4-ylboronic acid (820 mg, 6.67 mmol, 1.50 equiv), PCy3 (156 mg, 0.56 mmol, 0.14 equiv), Pd2(dba)3 (220 mg, 0.24 mmol, 0.06 equiv), and K3PO4 (2.5 g, 11.79 mmol, 3.00 equiv) in 1,4-dioxane (10 mL) was placed in a 20-mL sealed tube under inert atmosphere stirred overnight at 100° C. in an oil bath, and then concentrated under vacuum. Purification via silica gel column (ethyl acetate/petroleum ether (1:20)) yielded 1.2 g (crude) of 4-(4-(trifluoromethyl)phenyl)pyridine as a yellow solid.

Workup

  1. customsealed tube under inert atmosphere
  2. concentrationconcentrated under vacuum
  3. customPurification via silica gel column (ethyl acetate/petroleum ether (1:20))

Sources & evidence

ORD record
ord-9aa2806e51804096ad13010781bee321
Source dataset
uspto-grants-2014_12
Patent number
US08916560B2

Reaction notes

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