Potassium Carbonate → HCID 11726606, compound

HRID 981167Notes

Reaction equation

HRID 981167 reaction equation
O[CH2:2][C:3]1[N:4]=[N:5][C:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1.P(Br)(Br)[Br:25].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C1C=CC=CC=1>[Br:25][CH2:2][C:3]1[N:4]=[N:5][C:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 24614Phosphorus tribromideHCID 10267209HCID 10267209, compound

Product 1

HCID 11726606HCID 11726606, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-hydroxymethyl-4-(3-nitrophenyl)-6-phenylpyridazine (0.86 g) in tetrahydrofuran (5 ml) was dropwise added to a solution of phosphorus tribromide (0.18 ml) in a mixture of tetrahydrofuran (10 ml) and benzene (5 ml) under ice cooling. After stirring for 4 hours at the same temperature, the reaction mixture was poured into ice-water (50 ml) adjusted to pH 9 with saturated aqueous potassium carbonate and extracted with ethyl acetate (50 ml). The separated organic layer was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The residue was subjected to a column chromatography on silica gel (50 g) and eluted with a mixture of chloroform and acetone (5:1 V/V). The fractions containing the desired compound were combined and concentrated under reduced pressure. The residue was recrystallized from diethyl ether to give 3-bromomethyl-4-(3-nitrophenyl)-6-phenylpyridazine (0.73 g).

Workup

  1. extractionextracted with ethyl acetate (50 ml)
  2. washThe separated organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. washeluted with a mixture of chloroform and acetone (5:1 V/V)
  6. additionThe fractions containing the desired compound
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-a491fa4ac0394424a19f6d5745bca62f
Source dataset
uspto-grants-1991_02
Patent number
US04990507

Reaction notes

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