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

HRID 45278

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

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

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

Sources & evidence

ORD record: ord-7ed85289fe0e4e46950710b1bf82c8b3
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541453B2

Linked notes

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