Hydroquinone → Ethyl 4-cyano-4-(2,3-difluorophenyl)butanoate

HRID 1481818Notes

Reaction equation

HRID 1481818 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][C:10]#[N:11].[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[CH2:14].C1(C=CC(O)=CC=1)O.[OH-].[K+]>>[C:10]([CH:9]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=1[F:1])[CH2:14][CH2:13][C:12]([O:16][CH2:17][CH3:18])=[O:15])#[N:11]

Participants

5

Reactant 4

HCID 785HydroquinoneHCID 8821Ethyl AcrylateHCID 14797Potassium HydroxideHCID 5189682,3-Difluorophenylacetonitrile

Product 1

HCID 68749022Ethyl 4-cyano-4-(2,3-difluorophenyl)butanoate

Conditions

Temperature
160 °C

Procedure

To a mixture of (2,3-difluorophenyl)acetonitrile (40.5 g, 265 mmol), ethyl acrylate (24 mL, 221 mmol), and hydroquinone (50 mg, 0.45 mmol) was added KOH (2 M in MeOH, 2.0 mL, 4.0 mmol) and the resulting mixture was heated at 160° C. for 16 h and then allowed to cool to ambient temperature. The crude mixture was purified by silica gel chromatography, eluting with a gradient of hexanes:EtOAc—100:0 to 50:50, to give the title compound. MS: m/z=207.9 (M−OEt).

Workup

  1. temperatureto cool to ambient temperature
  2. customThe crude mixture was purified by silica gel chromatography
  3. washeluting with a gradient of hexanes

Sources & evidence

ORD record
ord-912d1cf2484142beb33431d38eabaac2
Source dataset
uspto-grants-2016_08
Patent number
US09409916B2

Reaction notes

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