2-Bromo-5-fluoropyridine → 5-Fluoro-2-phenylpyridine

HRID 39514Notes

Reaction equation

HRID 39514 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[C:9]1([Mg]Br)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCCC1.CCOC(C)=O>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 27831712-Bromo-5-fluoropyridineHCID 178418255HCID 178418255, compound

Product 1

HCID 463149355-Fluoro-2-phenylpyridineYield 69.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-5-fluoropyridine (10.0 g, 56.82 mmol, Aldrich) in tetrahydrofuran (100 ml) was added tetrakis(triphenylphosphine)Pd complex and stirred for 10 min. Then, phenylmagnesium bromide (68.2 ml, 1.00 M in THF, 68.19 mmol) was added drop-wise at 0° C. The mixture was stirred overnight. Then the reaction was diluted with EtOAc (600 ml), and filtered. The filtrate was concentrated and purified by flash chromatography by eluting with 2% EtOAc-Hexane to obtain 6.8 g (69%) of 5-fluoro-2-phenylpyridine.

Workup

  1. stirringThe mixture was stirred overnight
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash chromatography
  5. washby eluting with 2% EtOAc-Hexane

Sources & evidence

ORD record
ord-4adc011c83a14595b9c9076f25ffe72d
Source dataset
uspto-grants-2013_09
Patent number
US08524911B2

Reaction notes

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