N-bromobutanimide → 3-(Bromomethyl)-6-phenylpyridazine

HRID 1054111Notes

Reaction equation

HRID 1054111 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.C1C(=O)N([Br:21])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:21][CH2:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 113787443-Methyl-6-phenylpyridazine

Product 1

HCID 667174453-(Bromomethyl)-6-phenylpyridazine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Synthesized using compound 65b (982 mg, 5.77 mmol), NBS (1.13 g, 6.35 mmol) and DBPO (70 mg, 0.29 mmol) in carbon tetrachloride according to Method A. Crude product was purified by flash chromatography on silica-gel using hexane/ethyl acetate (4:1) as eluent. Product was used directly in the next step without further characterization. Orange solid. Yield: 53 mg, 4%. (ESI): m/z=250.67 [M+H]+.

Workup

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel

Sources & evidence

ORD record
ord-e12083880c59418886cef06b3e62e0f5
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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