Acetic Acid → 3-Chloro-6-(2-fluorobenzyl)pyridazine

HRID 1419496Notes

Reaction equation

HRID 1419496 reaction equation
[OH-].[Li+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([C:15]1[N:16]=[N:17][C:18]([Cl:21])=[CH:19][CH:20]=1)C(OC)=O.C(O)(=O)C>CO>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:15]1[N:16]=[N:17][C:18]([Cl:21])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 54453091Methyl 2-(2-fluorophenyl)-2-(6-chloropyridazin-3-yl)acetate

Product 1

HCID 64045713-Chloro-6-(2-fluorobenzyl)pyridazineYield 77.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous solution of lithium hydroxide (2 g /10 ml of water) was added to a solution of methyl 2-(2-fluorophenyl)-2-(6-chloropyridazin-3-yl)acetate (4.25 g, 14.84 mmol) [prepared as described above] in methanol (30 ml). After 1.5 h, acetic acid (10 ml) was added and the stirring was continued overnight. The product was extracted into ether, and the extract was washed with water, aqueous NaHCO3, and brine, and dried over MgSO4. The solvent was removed in vacuo and the crude was chromatographed on a silica gel column (10% ethyl acetate in hexanes) to give 6-(2-fluorobenzyl)-3-chloropyridazine (2.56 g) as an oil.

Workup

  1. waitthe stirring was continued overnight
  2. extractionThe product was extracted into ether
  3. washthe extract was washed with water, aqueous NaHCO3, and brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed in vacuo
  6. customthe crude was chromatographed on a silica gel column (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d202639a6535496fa7abe20170396e09
Source dataset
uspto-grants-1999_03
Patent number
US05886178

Reaction notes

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