Acetonitrile → (3-Fluoropyridin-2-yl)acetonitrile

HRID 869178Notes

Reaction equation

HRID 869178 reaction equation
Cl[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9](#[N:11])[CH3:10].C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>C1(C)C=CC=CC=1>[F:8][C:7]1[C:2]([CH2:10][C:9]#[N:11])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 2724254Sodium bis(trimethylsilyl)amideHCID 27827912-Chloro-3-fluoropyridine

Product 1

HCID 19703484(3-Fluoropyridin-2-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 2-chloro-3-fluoropyridine (3.0 g, 23 mmol, 1.0 equiv) and acetonitrile (1.3 mL, 25 mmol, 1.1 equiv) in toluene (50 mL) was added sodium hexamethyldisilazide (NaHMDS) (2.0 M in THF, 13 mL, 25 mmol, 1.1 equiv). The resulting mixture was stirred for 2 hours at 0° C. and then partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc and the combined organic phases were washed with saturated NaCl, dried over Na2SO4 and concentrated in vacuo to provide the crude desired product as an oil which was used without further purification.

Workup

  1. custompartitioned between EtOAc and water
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organic phases were washed with saturated NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-382e158424224c7392b93d75b16605d6
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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