1,1-Dibromoethane → HCID 89853565, compound

HRID 931074Notes

Reaction equation

HRID 931074 reaction equation
[N:1]1[CH:6]=[C:5]([CH2:7][C:8]#[N:9])[CH:4]=[N:3][CH:2]=1.Br[CH:11](Br)[CH3:12].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C(OCC)(=O)C>[N:1]1[CH:6]=[C:5]([C:7]2([C:8]#[N:9])[CH2:12][CH2:11]2)[CH:4]=[N:3][CH:2]=1

Participants

7

Reactant 3

HCID 112011,1-DibromoethaneHCID 14798Sodium HydroxideHCID 20080445HCID 20080445, compound

Product 1

HCID 89853565HCID 89853565, compoundYield 22.1%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(pyrimidin-5-yl)acetonitrile (104 mg, 0.873 mmol), dibromoethane (113 μL, 1.31 mmol) and tetrabutylammonium bromide (65 mg, 0.23 mmol) dissolved in toluene was added an aqueous solution of sodium hydroxide (50%, 500 mg in 0.5 mL of water, 12.5 mmol). The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with ethyl acetate (2 mL), washed with water (0.5 mL×2) and brine (0.5 mL). The organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified via flash chromatography (0-80% ethyl acetate in heptanes) to afford 1-(pyrimidin-5-yl)cyclopropanecarbonitrile as a solid (28 mg, 22%). 1H NMR (500 MHz, CDCl3) δ 1.50-1.56 (m, 2H), 1.85-1.95 (m, 2H), 8.72 (s, 2H), 9.19 (s, 1H).

Workup

  1. washwashed with water (0.5 mL×2) and brine (0.5 mL)
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified via flash chromatography (0-80% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-a2d04c5608da4c62b40b8dad16ec9d70
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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