Cyanoacetic acid → Perfluorophenyl 2-cyanoacetate

HRID 2204460Notes

Reaction equation

HRID 2204460 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[OH:12].[C:13]([CH2:15][C:16](O)=[O:17])#[N:14].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[C:13]([CH2:15][C:16]([O:12][C:3]1[C:2]([F:1])=[C:7]([F:8])[C:6]([F:9])=[C:5]([F:10])[C:4]=1[F:11])=[O:17])#[N:14]

Participants

5

Reactant 3

HCID 9740Cyanoacetic acidHCID 10868DicyclohexylcarbodiimideHCID 13041Pentafluorophenol

Product 1

HCID 20402415Perfluorophenyl 2-cyanoacetateYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3,4,5,6-pentafluorophenol (1.08 g, 5.88 mmol) and 2-cyanoacetic acid (0.50 g, 5.9 mmol) in DCM (20 mL) was added DCC (1.21 g, 5.88 mmol). After stirring for about 4 h at ambient temperature, the reaction was concentrated under reduced pressure and then purified over silica gel (20 g) using DCM as the eluent to afford perfluorophenyl 2-cyanoacetate as a white solid (1.39 g, 94%): 1H NMR (400 MHz, CDCl3) δ 3.85 (s, 2H).

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. custompurified over silica gel (20 g)

Sources & evidence

ORD record
ord-168ae016ac0e453781d9e19f97d70e4f
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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