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

HRID 1010554Notes

Reaction equation

HRID 1010554 reaction equation
[OH-].[Na+].[F:3][C:4]1([F:18])[O:8][C:7]2[CH:9]=[CH:10][C:11]([C:13]3([C:16]#[N:17])[CH2:15][CH2:14]3)=[CH:12][C:6]=2[O:5]1.FC1(F)OC2C=CC(CC#N)=CC=2O1.BrCCCl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[F:18][C:4]1([F:3])[O:8][C:7]2[CH:9]=[CH:10][C:11]([C:13]3([C:16]#[N:17])[CH2:15][CH2:14]3)=[CH:12][C:6]=2[O:5]1

Participants

6

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 203113842,2-Difluoro-1,3-benzodioxole-5-acetonitrileHCID 673151521-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonitrile Sodium hydroxide

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

1-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonitrile 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. and 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-e7d387cfcb574f8f999027dd01f75bcd
Source dataset
uspto-grants-2011_07
Patent number
US07977322B2

Reaction notes

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