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

HRID 402553Notes

Reaction equation

HRID 402553 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 (2,2-difluoro-1,3-benzodioxol-5-yl)-acetonitrile (1.0 eq), 50 wt % aqueous KOH (5.0 eq) 1-bromo-2-chloroethane (1.5 eq), and Oct4NBr (0.02 eq) was heated at 70° C. for 1 hour. The reaction mixture was cooled, then worked up with MTBE and water. The organic phase was washed with water and brine. The solvent was removed to afford (2,2-difluoro-1,3-benzodioxol-5-yl)-cyclopropanecarbonitrile.

Workup

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

Sources & evidence

ORD record
ord-b31b38c8d06e404692822a02bc0a8745
Source dataset
uspto-grants-2014_06
Patent number
US08742122B2

Reaction notes

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