Ethyl Acetate → 2-(Trifluoromethyl)phenylacetonitrile

HRID 1843876Notes

Reaction equation

HRID 1843876 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([F:12])([F:11])[F:10].[C-:13]#[N:14].[Na+].C(OC(=O)C)C>CS(C)=O.CCCCCC>[F:10][C:9]([F:12])([F:11])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][C:13]#[N:14]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzene

Product 1

HCID 764352-(Trifluoromethyl)phenylacetonitrileYield 88.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8058HexaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 1-bromomethyl-2-trifluoromethyl-benzene (3.5 g, 14.641 mmol) in DMSO (18 mL) and sodium cyanide (1.076 g, 21.962 mmol) were taken in a flask and the flask was heated to 90° C. for 3 hours. The reaction was monitored by TLC (2% ethylacetate in hexane). The reaction mixture was partitioned between water and ethylacetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford 2.4 g of the crude product which was used in the next step without further purification.

Workup

  1. customThe reaction mixture was partitioned between water and ethylacetate
  2. washThe organic layer was washed with brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-083f6a605b644a6ea5d6741bbb90912e
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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