1,2-Dibromoethane → 1-(6-Chloropyridazin-3-yl)cyclopropane-1-carbonitrile

HRID 1528568Notes

Reaction equation

HRID 1528568 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[N:9]=[N:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.Br[CH2:14][CH2:15]Br>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.C(#N)C>[Cl:3][C:4]1[N:9]=[N:8][C:7]([C:10]2([C:11]#[N:12])[CH2:15][CH2:14]2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 224447672-(6-Chloropyridazin-3-yl)acetonitrile

Product 1

HCID 866961331-(6-Chloropyridazin-3-yl)cyclopropane-1-carbonitrile

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

Aqueous NaOH solution (50%, 5 mL) was added to a solution of (6-chloro-pyridazin-3-yl)-acetonitrile (0.21 g), 1,2-dibromoethane (0.14 mL), and benzyltributylammonium chloride (0.43 g) in acetonitrile (5 mL) at room temperature. The resulting mixture was stirred at room temperature for 4 h and was then extracted with ethyl acetate. The combined extracts were washed with brine and dried (MgSO4). The solvent was evaporated and the residue was chromatographed on silica gel (cyclohexane/ethyl acetate 1:1→0:1) to give the title compound as a solid. Yield: 0.14 g (57% of theory); LC (method 1): tR=1.12 min; Mass spectrum (ESI+): m/z=180/182 (Cl) [M+H]+.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated
  5. customthe residue was chromatographed on silica gel (cyclohexane/ethyl acetate 1:1→0:1)

Sources & evidence

ORD record
ord-5ac3737e11644e538843f74cf2f5d034
Source dataset
uspto-grants-2015_07
Patent number
US09090605B2

Reaction notes

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