Water → 2-Phenylpyridine

HRID 1067915Notes

Reaction equation

HRID 1067915 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]1([Mg]Cl)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:8]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 79772-ChloropyridineHCID 178478979HCID 178478979, compound

Product 1

HCID 138872-PhenylpyridineYield 98.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

216.5 g (3.0 mol) of tetrahydrofuran (THF), 113.5 g (1.0 mol) of 2-chloropyridine and 0.24 g of Pd(dppf)Cl2 (0.03 mol %) are placed in a flask and heated to 50° C. while stirring. 510 g of phenylmagnesium chloride solution in THF (27% strength) are slowly metered in while cooling externally so that the temperature does not exceed 50° C. The mixture is then stirred for another 90 minutes at this temperature. It is slowly hydrolyzed with 250 g of water and allowed to cool to room temperature. After phase separation, the aqueous phase is stirred with 250 ml of tert-butyl methyl ether. After renewed phase separation, the organic phases combined and the reaction mixture is evaporated at 150 mbar. It is subsequently distilled at atmospheric pressure until a bottom temperature of 80° C. has been reached. The distillation residue is distilled at 10 mbar, giving 152.0 g of 2-phenylpyridine (98.1%), purity: 98.7% (according to GC).

Workup

  1. temperaturewhile cooling externally so that the temperature
  2. customdoes not exceed 50° C
  3. stirringThe mixture is then stirred for another 90 minutes at this temperature
  4. temperatureto cool to room temperature
  5. customAfter phase separation
  6. stirringthe aqueous phase is stirred with 250 ml of tert-butyl methyl ether
  7. customphase separation
  8. customthe reaction mixture is evaporated at 150 mbar
  9. distillationIt is subsequently distilled at atmospheric pressure until a bottom temperature of 80° C.
  10. distillationThe distillation residue is distilled at 10 mbar

Sources & evidence

ORD record
ord-df83252ebc404baca49f0a8efc794bba
Source dataset
uspto-grants-2001_06
Patent number
US06248892B1

Reaction notes

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