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

HRID 39446

Reaction equation

HRID 39446 reaction equation
[OH-].[Na+].[F:3][C:4]1([F:16])[O:8][C:7]2[CH:9]=[CH:10][C:11]([CH2:13][C:14]#[N:15])=[CH:12][C:6]=2[O:5]1.[CH2:17]([N+](CC)(CC)CC)[C:18]1C=CC=CC=1.[Cl-].BrCCCl>O>[F:16][C:4]1([F:3])[O:8][C:7]2[CH:9]=[CH:10][C:11]([C:13]3([C:14]#[N:15])[CH2:18][CH2:17]3)=[CH:12][C:6]=2[O:5]1

Participants

7

Reactant 5

HCID 312ChlorideHCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 17208BenzyltriethylammoniumHCID 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

Sodium hydroxide (50% aqueous solution, 10 mL) was slowly added to a mixture of crude (2,2-difluoro-benzo[1,3]dioxol-5-yl-acetonitrile, benzyltriethylammonium, chloride (3.00 g, 15.3 mmol), and 1-bromo-2-chloroethane (4.9 g, 38 mmol) at 70° C. The mixture was stirred overnight at 70° C. before the reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and evaporated to dryness to give crude 1-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonitrile, which was used directly in the next step.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-b5f7da59d0044b58b7f926938dd088e6
Source dataset
uspto-grants-2013_09
Patent number
US08524910B2

Linked notes

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