1-Bromo-2-Chloroethane → HCID 90332486, compound

HRID 595775Notes

Reaction equation

HRID 595775 reaction equation
[OH-].[Na+].[Br:3][C:4]1[N:9]=[C:8]([Cl:10])[C:7]([CH2:11][C:12]#[N:13])=[CH:6][CH:5]=1.Br[CH2:15][CH2:16]Cl>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:3][C:4]1[N:9]=[C:8]([Cl:10])[C:7]([C:11]2([C:12]#[N:13])[CH2:16][CH2:15]2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 90332435HCID 90332435, compound

Product 1

HCID 90332486HCID 90332486, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of NaOH (2.59 g, 64.8 mmol) in water (6 mL) was added 2-(6-bromo-2-chloropyridin-3-yl)acetonitrile (1.5 g, 6.48 mmol), tetrabutyl ammonium bromide (0.418 g, 1.296 mmol) and 1-bromo-2-chloroethane (1.079 mL, 12.96 mmol). The resulting mixture was heated to 50° C. and stirred for 2 h, extracted with ethyl acetate (2×30 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified using column chromtography (eluted with 0-20% ethyl acetate in hexane) to give 1-(6-bromo-2-chloropyridin-3-yl)cyclopropanecarbonitrile (850 mg, yield: 51%) MS (M+H)+: 258.

Workup

  1. extractionextracted with ethyl acetate (2×30 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified
  6. washcolumn chromtography (eluted with 0-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-a503ee699f324a5b9d7f5ce1dd14643c
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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