Acetonitrile → 2-(6-Bromopyridin-2-yl)acetonitrile

HRID 2060607Notes

Reaction equation

HRID 2060607 reaction equation
[CH3:1][C:2]#[N:3].C([Li])CCC.Br[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[N:11]=1>C1COCC1>[Br:16][C:12]1[N:11]=[C:10]([CH2:1][C:2]#[N:3])[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 122742,6-DibromopyridineHCID 178418339Butyllithium

Product 1

HCID 6428642-(6-Bromopyridin-2-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of MeCN (14.29 mL, 274 mmol) in THF (300 mL) at −78° C. was added n-butyllithium (2.5 Min hexanes, 100 mL, 251 mmol). After stirring for 30 minutes at −78° C., 2,6-dibromopyridine (18.0 g, 76 mmol) in THF (100 mL) was added. The reaction was stirred at −78° C. for 45 minutes, warmed to room temperature over 45 minutes, and quenched with water. The mixture was extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried (MgSO4), and concentrated in vacuo. Flash chromatography (silica, 0-40% ethyl acetate/hexanes) afforded the title compound as a yellow solid. LRMS (APCI) calcd for C7H6BrN2 [M+H]+ 197, found 197.

Workup

  1. stirringThe reaction was stirred at −78° C. for 45 minutes
  2. temperaturewarmed to room temperature over 45 minutes
  3. customquenched with water
  4. extractionThe mixture was extracted with ethyl acetate (2×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4dd0fed5a09b46c78b803ff5c85ea27f
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

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