1-Bromo-2-Chloroethane → 1-(4-Ethynylphenyl)cyclopropane-1-carbonitrile

HRID 557955Notes

Reaction equation

HRID 557955 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1)#[CH:2].Br[CH2:13][CH2:14]Cl.[OH-].[Na+].O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:10]#[N:11])[CH2:14][CH2:13]2)=[CH:5][CH:4]=1)#[CH:2]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 16069314(4-Ethynylphenyl)acetonitrileHCID 23719242Sodium hydroxide--water (1/1/1)

Product 1

HCID 866022871-(4-Ethynylphenyl)cyclopropane-1-carbonitrileYield 92.7%

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Conditions

Temperature
50 °C

Procedure

A mixture of (4-ethynylphenyl)acetonitrile (1.0 g, 0.0071 mol), 1-bromo-2-chloro-ethane (1200 μL, 0.014 mol), benzyltriethylammonium chloride (0.1 g, 0.0004 mol) and 1 ml of 50% NaOH water (w/v) was heated at 50° C. for 4 hours. The product was extracted with EtOAc and the combined organic phases were washed with water and brine successively, dried over Na2SO4, filtered, and concentrated in-vacuo to afford 1.1 g of the desired product, which was used in the following step without further purification.

Workup

  1. extractionThe product was extracted with EtOAc
  2. washthe combined organic phases were washed with water and brine successively
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-c48a2a1e58bc4dd789322b538095fac7
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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