1,2-Dibromoethane → Ethyl 1-(pyridazin-3-yl)cyclopropanecarboxylate

HRID 931173Notes

Reaction equation

HRID 931173 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:4]=1.Br[CH2:16][CH2:17]Br>CS(C)=O>[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:17][CH2:16]2)[N:4]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 52911166Ethyl 2-(pyridazin-3-yl)acetate

Product 1

HCID 89853348Ethyl 1-(pyridazin-3-yl)cyclopropanecarboxylateYield 43.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (60% suspension in mineral oil, 830 mg, 21.66 mmol) was washed with petroleum ether under a nitrogen atmosphere to remove the mineral oil. Dimethylsulfoxide (10 mL) was added and the resulting suspension was stirred for 5 min before adding ethyl 2-(pyridazin-3-yl)acetate (600 mg, 3.61 mmol) and 1,2-dibromoethane (2.03 g, 10.83 mmol) dissolved in dimethylsulfoxide (10 mL) at 10° C. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The mixture was partitioned between a saturated aqueous solution of ammonium chloride and ethyl acetate. The organics were dried over sodium sulfate and concentrated under reduced pressure. The resulting crude material was purified via column chromatography (100-200 silica gel mesh, 50-60% ethyl acetate in petroleum ether) to afford ethyl 1-(pyridazin-3-yl)cyclopropanecarboxylate (300 mg). MS (ES+APCI) (M+H) 193.0.

Workup

  1. customto remove the mineral oil
  2. additionDimethylsulfoxide (10 mL) was added
  3. stirringstirred for 2 h
  4. customThe mixture was partitioned between a saturated aqueous solution of ammonium chloride and ethyl acetate
  5. dry with materialThe organics were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting crude material was purified via column chromatography (100-200 silica gel mesh, 50-60% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-f6c177041ba74bf2af87d5fe8f0d48d6
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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