1,4-Dibromobutane → HCID 86694108, compound

HRID 707228Notes

Reaction equation

HRID 707228 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9]#[N:10])=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:12][CH2:13][CH2:14][CH2:15]Br.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1>[Cl:1][C:2]1[C:7]([C:8]2([C:9]#[N:10])[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 147395432-(2-Chloropyridin-3-yl)acetonitrile

Product 1

HCID 86694108HCID 86694108, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Chloropyridin-3-yl)acetonitrile (0.280 g, 1.835 mmol) was dissolved in dry tetrahydrofuran (1.5 mL) under nitrogen and cooled in an ice bath. 1,4-Dibromobutane (0.220 ml, 1.842 mmol) was added followed by dropwise addition of sodium bis(trimethylsilyl)amide (1.0 M in tetrahydrofuran, 4.5 ml, 4.50 mmol). The mixture was stirred for 20 minutes then quenched by addition of saturated ammonium chloride (10 mL). Water (100 mL) and ethyl acetate (200 mL) were added and the phases mixed and separated. The organic was dried with magnesium sulfate and evaporated to dryness under reduced pressure. Purification using silica chromatography (hexane to ethyl acetate gradient) gave the desired 1-(2-chloropyridin-3-yl)cyclopentanecarbonitrile (0.252 g, 1.219 mmol, 66.4% yield).

Workup

  1. temperaturecooled in an ice bath
  2. customthen quenched by addition of saturated ammonium chloride (10 mL)
  3. additionWater (100 mL) and ethyl acetate (200 mL) were added
  4. additionthe phases mixed
  5. customseparated
  6. dry with materialThe organic was dried with magnesium sulfate
  7. customevaporated to dryness under reduced pressure
  8. customPurification

Sources & evidence

ORD record
ord-ee49a0b97da04fe2ab5a0ad1087ed3d8
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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