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

HRID 578879Notes

Reaction equation

HRID 578879 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

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydrideHCID 27627292-(4,6-dichloropyridin-3-yl)acetonitrile

Product 1

HCID 89544502HCID 89544502, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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).

Workup

  1. customAt 0° C
  2. stirringThe reaction mixture was stirred 30 min at 0° C.
  3. customovernight
  4. customat rt
  5. customIt was quenched with aq NH4Cl
  6. customThe organic layer was separated
  7. dry with materialdried with Na2SO4
  8. filtrationthen filtrated
  9. concentrationThe filtrate was concentrated
  10. customThe crude product was purified by flash chromatography (Solvent: Cyclohexane/EtOAc 3/1)

Sources & evidence

ORD record
ord-7200d058d4a246489d96b9fc2c3d984c
Source dataset
uspto-grants-2015_05
Patent number
US09040708B2

Reaction notes

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