1,2-Dibromopropane → 1-[2-(Trifluoromethyl)phenyl]cyclobutanecarbonitrile

HRID 252279Notes

Reaction equation

HRID 252279 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]#[N:11].Br[CH2:15][CH:16](Br)[CH3:17].[H-].[Na+]>CCOCC.CS(C)=O>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([C:10]#[N:11])[CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 65531,2-DibromopropaneHCID 24758Sodium hydrideHCID 764352-(Trifluoromethyl)phenylacetonitrile

Product 1

HCID 596809531-[2-(Trifluoromethyl)phenyl]cyclobutanecarbonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 12.6 g of (2-trifluoromethyl-phenyl)-acetonitrile and 7.6 ml of 1,2-dibromopropane in 36 ml ether were added slowly through a dropping funnel to a suspension of 3.62 g of sodium hydride in 85 ml DMSO at 0° C. After addition, the ice-water bath was allowed to warm up to room temperature slowly and the reaction mixture was stirred at room temperature overnight. The reaction was carefully quenched with isopropyl and H2O. The suspension became clear. The organic layer was separated, and the aqueous layer was extracted twice with ether. The combined organic extracts were combined, dried and concentrated by evaporation in a vacuum. The residue was purified by column chromatography on silica-gel (EtOAc-hexane 2%-4%) to yield 8.5 g of product as a white solid.

Workup

  1. additionAfter addition
  2. customThe reaction was carefully quenched with isopropyl and H2O
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted twice with ether
  5. customdried
  6. concentrationconcentrated by evaporation in a vacuum
  7. customThe residue was purified by column chromatography on silica-gel (EtOAc-hexane 2%-4%)

Sources & evidence

ORD record
ord-ec499535d962491f92e068fa76458fe9
Source dataset
uspto-grants-2011_01
Patent number
US07868031B2

Reaction notes

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