Phosphorus oxybromide → 3-Bromo-6-phenylpyridazine

HRID 915643Notes

Reaction equation

HRID 915643 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

6-Phenylpyridazin-3-ol (5.0 g, 29.06 mmol) is dissolved in toluene (100 mL) and heated to 90° C. Phosphorous oxybromide (25 g, 87.19 mmol) is added in several portions and the reaction is heated for 30 minutes. The resulting yellow solution is cooled to room temperature, poured onto ice water, and extracted with ethyl acetate. The organic layers are further washed with water and 1M sodium hydroxide, dried over magnesium sulfate, filtered, and evaporated to a yellow solid. Recrystallization from CHCl3 gives 2.17 g of 3-bromo-6-phenylpyridazine.

Workup

  1. temperaturethe reaction is heated for 30 minutes
  2. temperatureThe resulting yellow solution is cooled to room temperature
  3. additionpoured onto ice water
  4. extractionextracted with ethyl acetate
  5. washThe organic layers are further washed with water and 1M sodium hydroxide
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to a yellow solid
  9. customRecrystallization from CHCl3

Sources & evidence

ORD record
ord-c2f2d929c2a14179a7541ef1fd52ea7d
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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