2,3-Dibromopyridine → 3-Bromo-2-phenethyl-pyridine

HRID 520989Notes

Reaction equation

HRID 520989 reaction equation
[Br-].[CH2:2]([Zn+])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[C:12]1[C:17]([Br:18])=[CH:16][CH:15]=[CH:14][N:13]=1>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.O1CCCC1>[Br:18][C:17]1[C:12]([CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 8171022,3-DibromopyridineHCID 178419778HCID 178419778, compound

Product 1

HCID 582943973-Bromo-2-phenethyl-pyridine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (2.0 g) is added to a flask charged with a stir bar, phenethylzinc bromide (0.5 mol/L in tetrahydrofuran, 100 mL), 2,3-dibromopyridine (10.50 g), and tetrahydrofuran (100 ml) and kept under argon atmosphere at room temperature. The resulting mixture is stirred at room temperature for 3 h and at 40° C. for another 16 h. After cooling the mixture to room temperature, the solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→75:25) to afford the title compound as an oil that solidified upon treatment with ether. Yield: 9.32 g (81% of theory); LC (method 1): tR=4.28 min; Mass spectrum (ESI+): m/z=262/264 (Br) [M+H]+.

Workup

  1. additioncharged with a stir bar
  2. customkept under argon atmosphere at room temperature
  3. temperatureAfter cooling the mixture to room temperature
  4. customthe solvent is evaporated
  5. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→75:25)

Sources & evidence

ORD record
ord-e84d04f29b014e82b634c221a6f99727
Source dataset
uspto-grants-2016_05
Patent number
US09328072B2

Reaction notes

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