Potassium Hydroxide → 1-(2,2-Difluorobenzo[D][1,3]dioxol-5-YL)cyclopropanecarbonitrile

HRID 2410392Notes

Reaction equation

HRID 2410392 reaction equation
[F:1][C:2]1([F:14])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11][C:12]#[N:13])=[CH:10][C:4]=2[O:3]1.[OH-].[K+].[CH3:17][C:18](OC)(C)C>O>[F:14][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:12]#[N:13])[CH2:18][CH2:17]3)=[CH:10][C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 15413tert-Butyl methyl etherHCID 203113842,2-Difluoro-1,3-benzodioxole-5-acetonitrile

Product 1

HCID 574461501-(2,2-Difluorobenzo[D][1,3]dioxol-5-YL)cyclopropanecarbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of compound 20 (1.0 eq), 50 wt % aqueous KOH (5.0 eq) 1-bromo-2-chloroethane (1.5 eq), and Oct4NBr (0.02 eq) is heated at 70° C. for 1 h. The reaction mixture is cooled then worked up with MTBE and water. The organic phase is washed with water and brine then the solvent is removed to afford compound 21.

Workup

  1. temperatureThe reaction mixture is cooled
  2. washThe organic phase is washed with water and brine
  3. customthe solvent is removed

Sources & evidence

ORD record
ord-13405cf452f44f90817a6619526accd0
Source dataset
uspto-grants-2014_08
Patent number
US08816093B2

Reaction notes

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