2,6-Difluoropyridine → 2-fluoro-6-phenylpyridine

HRID 915639Notes

Reaction equation

HRID 915639 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1.[C:9]1([Li])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCCC1>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1

Participants

4

Reactant 2

HCID 739342,6-DifluoropyridineHCID 178506676HCID 178506676, compound

Product 1

HCID 27628912-fluoro-6-phenylpyridineYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

Dissolve 2,6-difluoropyridine (5.0 mL, 5.51 mmol) in anhydrous tetrahydrofuran (30 mL) and cool to −40° C. Add a solution of phenyl lithium (1.8 M hexanes, 30.6 mL) dropwise over 5 minutes. Stir the resulting purple reaction at −40° C. for 30 minutes and bring to room temperature. Quench the reaction with water and extract the solution with ethyl acetate several times. Combine the organic extracts, dry over magnesium sulfate, filter and evaporate onto silica gel. Purification by flash column chromatography yields 2-fluoro-6-phenylpyridine 1.0 g (12%) as a yellow oil.

Workup

  1. customthe resulting purple reaction at −40° C. for 30 minutes
  2. custombring to room temperature
  3. customQuench
  4. customthe reaction with water
  5. extractionextract the solution with ethyl acetate several times
  6. dry with materialCombine the organic extracts, dry over magnesium sulfate
  7. filtrationfilter
  8. customevaporate onto silica gel
  9. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-540c9d8ea5c446fdb7b0f8573ca3d5d9
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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