1,2-Dibromoethane → 1-(3-Methoxyphenyl)cyclopropane-1-carbonitrile

HRID 516854Notes

Reaction equation

HRID 516854 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.[OH-].[CH2:13]([N+](CCCC)(CCCC)CCCC)[CH2:14]CC.[OH-].[Na+].BrCCBr>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([C:10]#[N:11])[CH2:14][CH2:13]2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 88310(3-Methoxyphenyl)acetonitrileHCID 2723671Tetrabutylammonium Hydroxide

Product 1

HCID 510639591-(3-Methoxyphenyl)cyclopropane-1-carbonitrile

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(3-methoxyphenyl)acetonitrile (6.5 g, 44.1 mmol), 40% aq tetrabutylammonium hydroxide (4.5 ml) and 50% aq NaOH (30 ml) in toluene (30 ml) was added 1,2-dibromoethane (10 ml, 116 mmol) at room temperature. The reaction mixture was stirred for 16 hours, diluted with EtOAc and washed with water and brine. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a short silica gel column (hex:ethyl acetate, 9:1) to give the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography on a short silica gel column (hex:ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-82bcf11139104b1f98dfbab995571ba4
Source dataset
uspto-grants-2015_08
Patent number
US09115072B2

Reaction notes

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