1-Bromo-2-Chloroethane → 1-(5-Bromopyridin-3-yl)cyclopropane-1-carbonitrile

HRID 712758Notes

Reaction equation

HRID 712758 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[N:6][CH:7]=1.Br[CH2:12][CH2:13]Cl.CCOC(C)=O>[OH-].[Na+].[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:9]#[N:10])[CH2:13][CH2:12]2)[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 8857Ethyl AcetateHCID 150054172-(5-Bromopyridin-3-yl)acetonitrile

Product 1

HCID 670560001-(5-Bromopyridin-3-yl)cyclopropane-1-carbonitrileYield 55%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

To a suspension of (5-bromo-pyridin-3-yl)-acetonitrile (1.0 g, 5.1 mmol) in 50% NaOH (20 mL) is added 1-bromo-2-chloro-ethane (764 mg, 5.33 mmol) and benzyl triethylammonium chloride (15 mg, 0.11 mmol). The resultant mixture is heated to 60° C. for 2 h. After cooling down to room temperature, EtOAc is added and extracted. The organic layers are combined and washed with brine, dried over Na2SO4, filtered and concentrated. The product is purified by column to afford 626 mg 1-(5-bromo-pyridin-3-yl)-cyclopropanecarbonitrile (55% yield).

Workup

  1. extractionextracted
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product is purified by column

Sources & evidence

ORD record
ord-aa323929ec944714b45fc2cd68f8b208
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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