5-Bromo-2-(trifluoromethyl)pyridine → 5-Ethenyl-2-(trifluoromethyl)pyridine

HRID 1481368Notes

Reaction equation

HRID 1481368 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1.[CH2:12](C([Sn])=C(CCCC)CCCC)[CH2:13]CC>CN(C=O)C.C1COCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:4]=[CH:3][C:2]([CH:12]=[CH2:13])=[CH:7][N:6]=1

Participants

6

Reactant 2

HCID 27611975-Bromo-2-(trifluoromethyl)pyridineHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 574168485-Ethenyl-2-(trifluoromethyl)pyridineYield 52.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

The title compound was prepared by following general procedure 2. 5-Bromo-2-trifluoromethylpyridine (2.0 g, 8.8 mmol) was dissolved in DMF:THF (3:1, 12 mL). Tributylvinyltin (3.0 g, 9.68 mmol) and Pd(PPh3)4 (0.135 g, 0.11 mmol) was added to this solution at RT under nitrogen and was heated at 100° C. for 2 h. After completion of the reaction (TLC), the reaction mixture was cooled to RT and diluted with water (120 mL) and extracted with ethyl acetate (3×100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure using rotary evaporator below 40° C. The crude was purified through column chromatography (2% ethylacetate:hexane in silica 100-200 mesh, Diameter of column—5.0 cm, Height of silica—approx. 5 inch) to provide 2-(trifluoromethyl)-5-vinylpyridine as a light yellow oil (0.8 g, 52% yield).

Workup

  1. customThe title compound was prepared
  2. customAfter completion of the reaction (TLC)
  3. temperaturethe reaction mixture was cooled to RT
  4. extractionextracted with ethyl acetate (3×100 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customevaporator below 40° C
  8. customThe crude was purified through column chromatography (2% ethylacetate:hexane in silica 100-200 mesh, Diameter of column—5.0 cm, Height of silica—approx. 5 inch)

Sources & evidence

ORD record
ord-ff78a147091845b2ad2e1385373bee6f
Source dataset
uspto-grants-2016_08
Patent number
US09409910B2

Reaction notes

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