Toluene → Methyl 1-(2-cyanophenyl)cyclopropanecarboxylate

HRID 2191904Notes

Reaction equation

HRID 2191904 reaction equation
Br[CH2:2][CH2:3]Br.[OH-].[Na+].C1(C)C=CC=CC=1.[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:23]([O:25][CH3:26])=[O:24])#[N:15]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1([C:23]([O:25][CH3:26])=[O:24])[CH2:3][CH2:2]1)#[N:15]

Participants

7

Reactant 4

HCID 1140TolueneHCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 1512623Methyl(2-cyanophenyl)acetate

Product 1

HCID 59470618Methyl 1-(2-cyanophenyl)cyclopropanecarboxylateYield 65.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

Tetra-n-butylammonium bromide (1.5 g), 1,2-dibromoethane (6.5 g) and aqueous 50% sodium hydroxide solution (20 mL) were added to a toluene (40 mL) solution of methyl 2-cyanophenylacetate (4.0 g), and stirred at room temperature for 1 hour. Water was added to the reaction liquid, and extracted with ethyl acetate. The organic layer was washed with saturated saline water, then dried with anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The crude product was purified through silica gel column chromatography (hexane/ethyl acetate) to give the entitled compound as a colorless solid (3.0 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated away under reduced pressure
  5. customThe crude product was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6113038d1c54459594a4643a827c32ea
Source dataset
uspto-grants-2012_12
Patent number
US08329711B2

Reaction notes

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