1-Bromo-2-Chloroethane → 1-(6-Chloropyridin-3-yl)cyclopropane-1-carbonitrile

HRID 2246780Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:14][CH2:15]Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2([C:9]#[N:10])[CH2:15][CH2:14]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a room temperature solution of (6-chloropyridin-3-yl)acetonitrile from Step 2 (6.1 g) in a solution of 9.9 mL of sodium hydroxide (50% in water W/W) were added 1-bromo-2-chloroethane (5.3 mL) and benzyltriethylammonium chloride (273 mg). The mixture was heated at 60° C. overnight. The reaction mixture was cooled to room temperature, poured into water (100 mL) and extracted with ethyl acetate (200 mL). The extracts were washed with saturated aqueous ammonium chloride and brine. Then dried with magnesium sulfate and the solvent removed in vacuo. The residue was purified by swish using diethyl ether and hexanes to yield the title compound.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with ethyl acetate (200 mL)
washThe extracts were washed with saturated aqueous ammonium chloride and brine
dry with materialThen dried with magnesium sulfate
customthe solvent removed in vacuo
customThe residue was purified

Sources & evidence

ORD record: ord-fc7d51ca2e75470c8f68eb451e51f013
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687524B2

Reaction notes

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