Iodoethane → (3-Cyano-4-fluoro-phenyl)-acetic acid ethyl ester

HRID 82190Notes

Reaction equation

HRID 82190 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:10][C:11]([OH:13])=[O:12])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].C(=O)([O-])[O-].[K+].[K+].[CH2:20](I)[CH3:21]>CN(C=O)C>[CH2:20]([O:12][C:11](=[O:13])[CH2:10][C:5]1[CH:6]=[CH:7][C:8]([F:9])=[C:3]([C:1]#[N:2])[CH:4]=1)[CH3:21]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 27739352-(3-Cyano-4-fluorophenyl)acetic acid

Product 1

HCID 70817504(3-Cyano-4-fluoro-phenyl)-acetic acid ethyl esterYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of (3-cyano-4-fluoro-phenyl)-acetic acid (500 mg, 2.79 mmol) (Preparation 126) and potassium carbonate (770 mg, 5.58 mmol) in DMF (5 mL) was added ethyl iodide (0.89 mL, 11.16 mmol) and the reaction mixture stirred at room temperature for 4 hours. The crude reaction mixture was poured onto water (10 mL) and extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with water (5×10 mL), brine (10 mL), dried over sodium sulphate, filtered and concentrated under reduced pressure to afford the title compound as an off-white solid in 87% yield, 500 mg.

Workup

  1. customThe crude reaction mixture
  2. additionwas poured onto water (10 mL)
  3. extractionextracted with ethyl acetate (3×15 mL)
  4. washThe combined organic layers were washed with water (5×10 mL), brine (10 mL)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0fec2b3a39854371bfeb32d1e842237a
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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