2-(Tributylstannyl)pyridine → HCID 22235107, compound

HRID 1743640Notes

Reaction equation

HRID 1743640 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1Br.C([Sn](CCCC)(CCCC)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)CCC>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.Cl[Pd]Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1

Participants

4

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 222351065-Bromo-2,4-difluorobenzotrifluoride

Product 1

HCID 22235107HCID 22235107, compound

Reagents, catalysts & solvents 1

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst

Procedure

2,4-Difluoro-5-(trifluoromethyl)bromobenzene (2.0 g, 7.7 mmol), 2-tributylstannylpyridine, and Bis(triphenylphosphine)palladium(II)chloride (0.16 g, 0.23 mmol) were added to 50 mL. xylenes and the mixture was heated to reflux for 16 hours. The reaction mixture was filtered through a silica gel plug and then purified with column chromatography to give 2-(2,4-difluoro-5-trifluoromethylphenyl)pyridine (1.4 g, 5.4 mmol). The product was confirmed by Mass Spectroscopy and 1H NMR.

Workup

  1. temperatureto reflux for 16 hours
  2. filtrationThe reaction mixture was filtered through a silica gel plug
  3. custompurified with column chromatography

Sources & evidence

ORD record
ord-ac858d54b27a4d21b057546ad6682c1f
Source dataset
uspto-grants-2006_03
Patent number
US07011897B2

Reaction notes

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