Pyridine → 2,5-Dibromo-3-nitropyridine

HRID 1711490Notes

Reaction equation

HRID 1711490 reaction equation
O[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([Br:11])=[CH:4][N:3]=1.CN(C)C=O.P(Br)(Br)([Br:19])=O.N1C=CC=CC=1>C1(C)C=CC=CC=1.O>[Br:19][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([Br:11])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 24613Phosphorus oxybromideHCID 178418997HCID 178418997, compound

Product 1

HCID 2984702,5-Dibromo-3-nitropyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent3×

Procedure

2-Hydroxy-3-nitro-5-bromopyridine (1 eq) was suspended in toluene (3 vol) and N,N-dimethylformamide (0.1 eq) was added. The mixture was protected from light. A solution of phosphorus oxybromide (1.2 eq) in toluene (2 vol) was added to the pyridine mixture over 1.5 h at about 90° C. and the reaction was aged for about 14 h at 90° C. The reaction mixture was cooled to room temperature and water (10 vol) and toluene (5 vol) were added. The layers were cut and the organic layer was washed with 1N NaOH (2×10 vol) and H2O (5 vol). The batch was concentrated under reduced pressure to yield the desired product.

Workup

  1. washthe organic layer was washed with 1N NaOH (2×10 vol) and H2O (5 vol)
  2. concentrationThe batch was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bdca5da0618b4b77a3a81d48fa9c5562
Source dataset
uspto-grants-2010_09
Patent number
US07790754B2

Reaction notes

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