1,2-Dibromoethane → Methyl 2-chloro-3-(1-cyanocyclopropyl)benzoate

HRID 2190454Notes

Reaction equation

HRID 2190454 reaction equation
[Cl:1][C:2]1[C:11]([CH2:12][C:13]#[N:14])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].Br[CH2:18][CH2:19]Br>CS(C)=O>[Cl:1][C:2]1[C:11]([C:12]2([C:13]#[N:14])[CH2:19][CH2:18]2)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 57386575HCID 57386575, compound

Product 1

HCID 67311674Methyl 2-chloro-3-(1-cyanocyclopropyl)benzoateYield 35%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Using Methyl 2-chloro-3-(cyanomethyl)benzoate (2.00 g, 9.54 mmol), sodium hydride (60% in oil, 1.14 g, 28.6 mmol), 1,2-dibromoethane (1.18 mL, 14.3 mmol) and dimethyl sulfoxide (20 mL) as starting materials, and in the same manner as in Example A1(ii), the title compound (787 mg, 35%) was obtained as a colorless oil.

Sources & evidence

ORD record
ord-0c20a0dedd004142a9cd4dc593376431
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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