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

HRID 1925112Notes

Reaction equation

HRID 1925112 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.C1C(=O)N([Br:16])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:8][C:5]1[N:4]=[N:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 2272543-Chloro-6-methylpyridazine

Product 1

HCID 230809253-(Bromomethyl)-6-chloropyridazineYield 26.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 3-Chloro-6-methyl-pyridazine 10A (5.12 g, 40 mmol) and NBS (8.90 g, 50 mmol) in CCl4 (300 mL) was refluxed under light (200 w) for 4 hours. The reaction mixture was cooled to room temperature and filtered. The solid residue was washed thoroughly with Cl4C and filtered. The filtrates was combined, concentrated to small volume and loaded on to a silica gel column. The column was eluted with 50% hexane/ethyl acetate to give 2.2 g of desired product (10B) which was dried in vacuum and used immediately in next step. ESI-MS:m/z 206.9 (M+H)+.

Workup

  1. filtrationfiltered
  2. washThe solid residue was washed thoroughly with Cl4C
  3. filtrationfiltered
  4. concentrationconcentrated to small volume
  5. washThe column was eluted with 50% hexane/ethyl acetate

Sources & evidence

ORD record
ord-7c68d6aba87540ff9a67999728bc88e6
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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