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

HRID 431839Notes

Reaction equation

[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[CH2:2].Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.O1CCCC1.C(=O)([O-])[O-].[K+].[K+]>O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[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)=[CH2:2]

Participants

Conditions

Temperature: 80 °C

Procedure

4-Vinyl-phenylboronic acid (10 g, 0.0676 mol), 2-bromopyridine (12.64 g, 0.08 mol), tetrahydrofuran (100 ml), 2M potassium carbonate aqueous Solution (26 ml), and tetrakis(triphenylphosphine) palladium (Pd(Ph3)4, 0.06 g, 1 mol %) were placed into 250 ml of 2-necked round-bottomed flask under N2. The reaction mixture was refluxed at 80° 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 (1/9) to yield 2-(4-vinyl-phenyl)pyridine (90%). mp: 19.3° C.; bp: 115° C./1 mmHg; 1H-NMR, 13C-NMR, FT-IR, GC and Mass spectra were shown in FIGS. 1-5.

Workup

extractionThe reaction mixture was extracted with ether (3×150 ml)
dry with materialthe ether layer was then dried over magnesium sulfate (10 g)
customThe dried ether layer was evaporated in vacuo to dryness
custompurified further by column chromatography on silica gel with eluting hexane/ethylacetate (1/9)

Sources & evidence

ORD record: ord-3de53174df9a4f3ebae716d319707fd9
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06660821B2

Reaction notes

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