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

HRID 716884Notes

Reaction equation

HRID 716884 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-94a26e97c9944941ad37f8b9a4279be0
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

Loading…