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

HRID 1853107Notes

Reaction equation

HRID 1853107 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-9ebab3cff550460486228362050a6911
Source dataset
uspto-grants-2015_02
Patent number
US08962632B2

Reaction notes

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