3-Nitrophenylboronic Acid → 3-Chloro-6-(3-nitrophenyl)pyridazine

HRID 1835438Notes

Reaction equation

HRID 1835438 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[N+:9]([C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1)([O-:11])=[O:10].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:9]([O-:11])=[O:10])[CH:17]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 673313,6-Dichloropyridazine

Product 1

HCID 122575043-Chloro-6-(3-nitrophenyl)pyridazineYield 10.4%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 3,6-dichloropyridazine (2.98 g), 3-nitrophenylboronic acid (1.67 g) and tetralis(triphenylphosphine)-palladium (578 mg) in 1,2-dimethoxyethane (30 ml) was added an aqueous solution of sodium carbonate (2M, 15 ml), and the mixture was stirred at 80° C. for 3 hours. The mixture was diluted with ethyl acetate, and then washed with water and brine. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by a silica gel column chromatography eluting with 30% ethyl acetate in n-hexane to give 3-chloro-6-(3-nitro-phenyl)-pyridazine (0.246 g, 10.4%).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by a silica gel column chromatography
  5. washeluting with 30% ethyl acetate in n-hexane

Sources & evidence

ORD record
ord-915d90480ff2448fb77c902850e540c0
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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