Toluene → Methyl 1-(2-cyanophenyl)cyclopropanecarboxylate

HRID 2088728Notes

Reaction equation

HRID 2088728 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

1.5 g of tetra-n-butylammonium bromide, 6.5 g of 1,2-dibromoethane and 20 mL of aqueous 50% sodium hydroxide solution were added to a toluene (40 mL) solution of 4.0 g of methyl 2-cyanophenylacetate, 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, 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 obtain 3.0 g of the entitled compound as a colorless compound.

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-cf35f67e7b0f47828aa07aa55cb5ffa9
Source dataset
uspto-grants-2013_05
Patent number
US08436004B2

Reaction notes

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