Ethyl Acetate → 2-Fluoro-5-(2,2,2-trifluoro-ethoxy)-benzonitrile

HRID 2089238Notes

Reaction equation

HRID 2089238 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[C:4]#[N:5].I[CH2:12][C:13]([F:16])([F:15])[F:14].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C>[F:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH2:12][C:13]([F:16])([F:15])[F:14])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 226124102-Fluoro-5-hydroxybenzonitrile

Product 1

HCID 674787712-Fluoro-5-(2,2,2-trifluoro-ethoxy)-benzonitrileYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-fluoro-5-hydroxy-benzonitrile (Alfa Aesar, 137 mg, 1.0 mmol) was added 2-iodo-1,1,1,-trifluoroethane (117 L, 1.2 mmol) and potassium carbonate (165 mg, 1.2 mmol) in DMF (20 mL) and stirred at RT for 24 hours. The reaction was dissolved into EtOAc and washed with water three times and the combined organic layers were dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica gel column chromatography using hexanes:ethyl acetate 5:1 to give the tile compound as white solid (105 mg, 48%).

Workup

  1. washwashed with water three times
  2. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c4c55e7bff9c4503b75ee8b44229ae9f
Source dataset
uspto-grants-2013_05
Patent number
US08436023B2

Reaction notes

Loading…