2-Bromopyridine → 2-(4-Vinylphenyl)pyridine

HRID 1265317Notes

Reaction equation

HRID 1265317 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=O.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.O1CCC[CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:5][CH:4]=1)=[CH2:20]

Participants

7

Reactant 4

HCID 79732-BromopyridineHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 117152892-(4-Vinylphenyl)pyridineYield 80%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

4-Formylphenylboronic acid (10.14 g, 0.0676 mol), 2-bromopyridine (12.64 g, 0.08 mol), tetrahydrofuran (100 ml), 2M potassium carbonate aqueous solution (26 ml), and palladium acetate (Pd(OAc)2, 0.04 g, 1 mol %) were placed into 250 ml of 2-necked round-bottomed flask under N2. The reaction mixture was refluxed at 90° C. for 24 hr and then poured in 200 ml of water in beaker. The reaction mixture was extracted with ether (3×150 ml) and the ether layer was then dried over magnesium sulfate (10 g) by stirring for 30 min. The dried ether layer was evaporated in vacuo to dryness and purified further by column chromatography on silica gel with eluting hexane/ethylacetate (1/5) to yield 2-(4-vinyl-phenyl)pyridine (80%).

Workup

  1. extractionThe reaction mixture was extracted with ether (3×150 ml)
  2. dry with materialthe ether layer was then dried over magnesium sulfate (10 g)
  3. customThe dried ether layer was evaporated in vacuo to dryness
  4. custompurified further by column chromatography on silica gel with eluting hexane/ethylacetate (1/5)

Sources & evidence

ORD record
ord-800000b357e94df1a00b495a15b6f337
Source dataset
uspto-grants-2003_04
Patent number
US06545159B2

Reaction notes

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