Water → HCID 69237907, compound

HRID 1522712Notes

Reaction equation

HRID 1522712 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][CH:3]=1.C([Li])CCC.F[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.O>CCOCC>[I:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 97462-FluoropyridineHCID 12208p-DiiodobenzeneHCID 178418339Butyllithium

Product 1

HCID 69237907HCID 69237907, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1,4-diiodobenzene (46.8 g, 142 mmol) in dry ether (450 mL) under argon was cooled in a salt-ice bath. n-Butyllithium (2.0 M in pentane, 72 mL, 142 mmol) was added, and the solution was stirred for 10 minutes. 2-Fluoropyridine (13 mL, 150 mmol) was added and the reaction was allowed to warm to room temperature over 2 hours. Water (500 mL) was added and the organic layer was separated. The aqueous layer was extracted with ether (3×200 mL) and the combined organic layers were washed with brine (1000 mL), dried over anhydrous magnesium sulfate, filtered, and the solvent completely removed. The residue was purified in two steps; first by column chromatography over silica using a dichloromethane/light petroleum mixture (1:1) followed by recrystallisation of the main fraction from a dichloromethane/light petroleum mixture to give (1) (17.0 g, 40%).

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted with ether (3×200 mL)
  3. washthe combined organic layers were washed with brine (1000 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent completely removed
  7. customThe residue was purified in two steps
  8. customfirst by column chromatography over silica using a dichloromethane/light petroleum mixture (1:1) followed by recrystallisation of the main fraction from a dichloromethane/light petroleum mixture

Sources & evidence

ORD record
ord-06a43e0143264190a7928ac1640ad1e7
Source dataset
uspto-grants-2015_07
Patent number
US09078330B2

Reaction notes

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