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

HRID 1393909Notes

Reaction equation

HRID 1393909 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-7b0b0d6ca2564e489803bbaaa3007934
Source dataset
uspto-grants-2008_03
Patent number
US07348322B2

Reaction notes

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