1-Bromo-2-Chloroethane → HCID 89544502, compound

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[CH:6][C:5]=1[CH2:11][C:12]#[N:13].Br[CH2:15][CH2:16]Cl>C1COCC1>[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[CH:6][C:5]=1[C:11]1([C:12]#[N:13])[CH2:16][CH2:15]1

Participants

Procedure

Sodium hydride (60% in mineral oil, 0.128 g, 3.21 mmol) was suspended in 0.5 ml THF. At 0° C. a solution of 2-(4,6-dichloro-3-pyridyl)acetonitrile (0.200 g, 1.07 mmol) in 1.7 ml THF was added drop wise. The reaction mixture was stirred until no gas evolution was detectable. It was then a red suspension. At 0° C. 1-Bromo-2-chloro-ethane (0.355 mL, 4.28 mmol) was added drop wise. The reaction mixture was stirred 30 min at 0° C. then overnight at rt. It was quenched with aq NH4Cl. The organic layer was separated and dried with Na2SO4 then filtrated. The filtrate was concentrated. The residue was a brown gum (260 mg). The crude product was purified by flash chromatography (Solvent: Cyclohexane/EtOAc 3/1). The desired product was isolated as a white solid (135 mg).