N-Fluorobenzenesulfonimide → 2-(3-Butoxyphenyl)-2-fluoroacetonitrile

HRID 62597Notes

Reaction equation

HRID 62597 reaction equation
C([Li])(C)(C)C.[CH2:6]([O:10][C:11]1[CH:12]=[C:13]([CH2:17][C:18]#[N:19])[CH:14]=[CH:15][CH:16]=1)[CH2:7][CH2:8][CH3:9].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:30])(=O)=O)=CC=1>C1COCC1>[CH2:6]([O:10][C:11]1[CH:12]=[C:13]([CH:17]([F:30])[C:18]#[N:19])[CH:14]=[CH:15][CH:16]=1)[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 588007N-FluorobenzenesulfonimideHCID 22158212(3-Butoxyphenyl)acetonitrileHCID 178418306HCID 178418306, compound

Product 1

HCID 711520922-(3-Butoxyphenyl)-2-fluoroacetonitrileYield 53.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tert-butyllithium (1268 uL; 2.16 mmol) is added dropwise to a solution of 2-(3-butoxyphenyl)acetonitrile (371 mg; 1.96 mmol) in THF (16 mL) at −78° C., under nitrogen atmosphere. The light yellow solution turned into orange and stirring is continued for 1 hour. A solution of N-fluorobenzenesulfonimide (618 mg; 1.96 mmol) in THF (2 mL) is added dropwise and the reaction is stirred at −78° C. for 2 hours. TLC (petroleum ether/EtAc 9:1) reveals no presence of starting material and two more apolar spots. The reaction is then quenched by adding 0.01N HCl, then more water is added and extracted with DCM (three times). The combined organic layers are dried over Na2SO4, filtered and evaporated. The crude residue is purified by flash chromatography (petroleum ether/EtAc, 99/1) affording 217 mg (53%) of 2-(3-butoxyphenyl)-2-fluoroacetonitrile as a colorless oil.

Workup

  1. stirringthe reaction is stirred at −78° C. for 2 hours
  2. customThe reaction is then quenched
  3. additionby adding 0.01N HCl
  4. additionmore water is added
  5. extractionextracted with DCM (three times)
  6. dry with materialThe combined organic layers are dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude residue is purified by flash chromatography (petroleum ether/EtAc, 99/1)

Sources & evidence

ORD record
ord-8b98d6d6bae14c9bb7f969e9a4b7b9cb
Source dataset
uspto-grants-2016_09
Patent number
US09447029B2

Reaction notes

Loading…