Potassium Carbonate → 2-Bromo-6-phenylpyridine

HRID 1041823Notes

Reaction equation

HRID 1041823 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.O>[Br: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

6

Reactant 3

HCID 11430Potassium CarbonateHCID 122742,6-DibromopyridineHCID 66827Phenylboronic Acid

Product 1

HCID 5686792-Bromo-6-phenylpyridineYield 34.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

In a 3-neck 1 L round-bottom flask fitted with a condenser, nitrogen inlet, and 2 stoppers was added 2,6-dibromopyridine (15.3 g, 64.58 mmol), phenylboronic acid (7.87 g, 64.58 mmol), and potassium carbonate (17:85 g, 129.16 mmol) in 228 mL of dimethoxyethane and 150 mL of water. Nitrogen was bubbled directly into the mixture for 15 minutes. Tetrakis(triphenylphosphine)palladium (0) was added (1.85 g, 1.60 mmol) and the reaction mixture was heated to reflux. The reaction was complete after 3 h of heating. It was cooled to room temperature and diluted with water and ethyl acetate. The layers were separated and the aqueous layer extracted with ethyl acetate. The organic layers were dried over magnesium sulfate, filtered, and evaporated. The material was purified by column chromatography eluting with 2% ethyl acetate/hexanes followed by vacuum distillation using a Kugelrohr collecting product at 150° C. 5.2 g of product was obtained (34%)

Workup

  1. customIn a 3-neck 1 L round-bottom flask fitted with a condenser, nitrogen inlet
  2. customNitrogen was bubbled directly into the mixture for 15 minutes
  3. additionTetrakis(triphenylphosphine)palladium (0) was added (1.85 g, 1.60 mmol)
  4. temperaturethe reaction mixture was heated to reflux
  5. temperatureof heating
  6. additiondiluted with water and ethyl acetate
  7. customThe layers were separated
  8. extractionthe aqueous layer extracted with ethyl acetate
  9. dry with materialThe organic layers were dried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customThe material was purified by column chromatography
  13. washeluting with 2% ethyl acetate/hexanes
  14. distillationfollowed by vacuum distillation
  15. customat 150° C

Sources & evidence

ORD record
ord-4b029eb15b1a4c63af1a03d7986c0a62
Source dataset
uspto-grants-2013_10
Patent number
US08557400B2

Reaction notes

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