Water → HCID 11967290, compound

HRID 1522723Notes

Reaction equation

HRID 1522723 reaction equation
C([Li])CCC.I[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([I:13])[CH:8]=1.F[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.O>CCOCC>[I:13][C:9]1[CH:8]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 97462-FluoropyridineHCID 12270Benzene, 1,3-diiodo-HCID 178418339Butyllithium

Product 1

HCID 11967290HCID 11967290, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

n-Butyllithium (2.0 M in cyclohexane, 8 cm3) was added dropwise to a solution of 1,3-diiodobenzene (5.19 g, 16 mmol) in ether (50 cm3), cooled in a salt-ice bath, and the solution was stirred for 10 minutes. 2-Fluoropyridine (1.4 cm3, 16 mmol) was added, at which the pale yellow cloudy solution turned dark brown, and the reaction was allowed to warm to room temperature over 1 hour. Water (50 cm3) and ether (20 cm3) were added, and the layers were separated. The aqueous layer was extracted with ether (3×50 cm3). The combined organic extracts were washed with brine (150 cm3), and dried over magnesium sulfate. The solvent was removed to leave a brown oil. Purification of the crude product by column chromatography over silica using dichloromethane: light petroleum (1:1) as eluent gave (15) as an orange oil (1.04 g, 24%).

Workup

  1. temperaturecooled in a salt-ice bath
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with ether (3×50 cm3)
  4. washThe combined organic extracts were washed with brine (150 cm3)
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed
  7. customto leave a brown oil
  8. customPurification of the crude product by column chromatography over silica

Sources & evidence

ORD record
ord-2e6f8b4819a94303b21421db97c7f215
Source dataset
uspto-grants-2015_07
Patent number
US09078330B2

Reaction notes

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