Sodium Iodide → 2-[4-(Trifluoromethyl)phenoxy]acetonitrile

HRID 1433193Notes

Reaction equation

HRID 1433193 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Br[CH2:13][C:14]#[N:15].C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CN(C=O)C>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[CH:5][C:6]([O:9][CH2:13][C:14]#[N:15])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 11534BromoacetonitrileHCID 678744-(Trifluoromethyl)phenol

Product 1

HCID 27775732-[4-(Trifluoromethyl)phenoxy]acetonitrileYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-trifluoromethyl-phenol (25.0 g, 0.154 mol), bromoacetonitrile (12.9 mL, 0.185 mol), sodium carbonate (32.7 g, 0.308 mol), and sodium iodide (23.1 g, 0.154 mol) in 214 mL of DMF was heated at 100° C. for 2 hours. The reaction was cooled, and partitioned between water and EtOAc. The organic layers were washed with water and brine, dried with Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:EtOAc, 4:1) to afford the title compound as a colorless oil (29.8 g, 96%). 1H NMR (400 MHz, CD3Cl) δ (ppm): 7.63 (d, 2H), 7.07 (d, 2H), 4.83 (s, 2H).

Workup

  1. temperatureThe reaction was cooled
  2. custompartitioned between water and EtOAc
  3. washThe organic layers were washed with water and brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by chromatography (silica, hexanes:EtOAc, 4:1)

Sources & evidence

ORD record
ord-be1ef2b50e5d4b30ae8cae2cff284910
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

Loading…