Phosphorus oxybromide → 3-Bromo-6-phenylpyridazine

HRID 2224733Notes

Reaction equation

HRID 2224733 reaction equation
[C:1]1([C:7]2[N:12]=[N:11][C:10](O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)([Br:16])=O>C1(C)C=CC=CC=1>[Br:16][C:10]1[N:11]=[N:12][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178515859HCID 178515859, compound

Product 1

HCID 111956883-Bromo-6-phenylpyridazineYield 31.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Dissolve 6-Phenylpyridazin-3-ol (5.0 g, 29.06 mmol) in toluene (100 mL) and heat to 90° C. Add phosphorous oxybromide (25 g, 87.19 mmol) in several portions and heat the reaction for 30 minutes. Cool the resulting yellow solution to room temperature, pour onto ice water, and extract with ethyl acetate. Further wash the organic layers with water and 1 M NaOH, dry over MgSO4, filter, and evaporate to a yellow solid. Recrystallization from CHCl3 gives 2.17 g of 3-bromo-6-phenylpyridazine.

Workup

  1. customthe reaction for 30 minutes
  2. temperatureCool the resulting yellow solution to room temperature
  3. additionpour onto ice water
  4. extractionextract with ethyl acetate
  5. washFurther wash the organic layers with water and 1 M NaOH
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. customevaporate to a yellow solid
  9. customRecrystallization from CHCl3

Sources & evidence

ORD record
ord-44d1eed93d32431f82d505d783562aac
Source dataset
uspto-grants-2008_05
Patent number
US07378447B2

Reaction notes

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