Sodium Carbonate → 2-Bromo-6-phenylpyridine

HRID 1457739Notes

Reaction equation

HRID 1457739 reaction equation
[C:1]1([C:7]2[NH:12][C:11](=O)[CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)([Br:16])=O.C(=O)([O-])[O-].[Na+].[Na+]>O>[Br:16][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:12]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24613Phosphorus oxybromideHCID 878896-Phenyl-2-pyridone

Product 1

HCID 5686792-Bromo-6-phenylpyridineYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-phenyl pyridone (3 g, 17.5 mmol; prepared according to Example 5) and phosphoryl bromide (7.2 g, 25.0 mmol) is heated to 100° C. for 5 h. The cooled mixture is poured into water (40 mL) and the pH is adjusted to 9 by addition of saturated aqueous sodium carbonate. Then the layers are separated and the aqueous layer is extracted with ethyl acetate (50 mL). The combined organic layers are dried with anhydrous magnesium sulphate and the solvent is evaporated in vacuo. The crude product is crystallized from aqueous ethanol. Subsequent purification by flash chromatography (silica gel, hexane/ethyl acetate 9/1 v/v) gives 2-bromo-6-phenyl pyridine (3.1 g, 76% of th.) as light brown crystals with mp 50° C.

Workup

  1. customThen the layers are separated
  2. extractionthe aqueous layer is extracted with ethyl acetate (50 mL)
  3. dry with materialThe combined organic layers are dried with anhydrous magnesium sulphate
  4. customthe solvent is evaporated in vacuo
  5. customThe crude product is crystallized from aqueous ethanol
  6. customSubsequent purification by flash chromatography (silica gel, hexane/ethyl acetate 9/1 v/v)

Sources & evidence

ORD record
ord-3aa055bcfa4540a6bc4263d3dc8e7684
Source dataset
uspto-grants-1998_12
Patent number
US05849758

Reaction notes

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