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

HRID 1442697Notes

Reaction equation

HRID 1442697 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.Br[CH2:18][CH2:19]Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.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])[CH2:19][CH2:18]3)=[CH:12][C:6]=2[O:5]1

Participants

6

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 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 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 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-07bbcca94a874b4aa4d0143bda3dc8bb
Source dataset
uspto-grants-2010_02
Patent number
US07659268B2

Reaction notes

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