1,2-Dibromoethane → HCID 89544407, compound

HRID 578884Notes

Reaction equation

HRID 578884 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([F:13])[C:9]=1[CH2:10][C:11]#[N:12].Br[CH2:15][CH2:16]Br>C1COCC1>[F:13][C:8]1[CH:7]=[N:6][CH:5]=[C:4]([F:3])[C:9]=1[C:10]1([C:11]#[N:12])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 84763458HCID 84763458, compound

Product 1

HCID 89544407HCID 89544407, compoundYield 174.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride 60% in mineral oil (3.35 g, 83.7 mmol) was suspended in 10 ml THF. At −10° C. a solution of 2-(3,5-difluoro-4-pyridyl)acetonitrile (4.30 g, 27.9 mmol) in 45 ml THF was added drop wise. The reaction mixture was stirred until no more gas evolution was visible. The reaction mixture was then a yellow suspension. At 0° C. 1,2-dibromoethane (9.71 mL, 112 mmol) was added drop wise. The reaction mixture was stirred 2 h at 0° C. then over night at rt. It was quenched with aq. NH4Cl, diluted with EtOAc. The organic layer was separated and dried with Na2SO4. Filtrated, the filtrate was evaporated. The residue gave a brown oil (8.75 g). The crude product was purified by flash chromatography (Solvent: Cyclohexane/EtOAc 1/1). The desired product was isolated as a colorless oil which crystallised upon standing (3.816 g).

Workup

  1. customAt 0° C
  2. stirringThe reaction mixture was stirred 2 h at 0° C.
  3. waitover night at rt
  4. customIt was quenched with aq. NH4Cl
  5. additiondiluted with EtOAc
  6. customThe organic layer was separated
  7. dry with materialdried with Na2SO4
  8. filtrationFiltrated
  9. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-3bd09e976e214d80b1871584b29ab967
Source dataset
uspto-grants-2015_05
Patent number
US09040708B2

Reaction notes

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