Sodium Carbonate → 2-Bromo-6-phenylpyridine

HRID 1108203Notes

Reaction equation

HRID 1108203 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 6) 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-2eafb7cfbb6e4962ab25104b8f9b0f10
Source dataset
uspto-grants-2000_05
Patent number
US06066597

Reaction notes

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