Sodium hydride → 4-(4-Fluoro-pyridin-2-yloxymethyl)-benzonitrile

HRID 1691050

Reaction equation

HRID 1691050 reaction equation
Cl[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][N:3]=1.[OH:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1.[H-].[Na+]>CN(C)C=O>[F:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([O:9][CH2:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 160549p-Cyanobenzyl alcoholHCID 27827922-Chloro-4-fluoropyridine

Product 1

HCID 592552704-(4-Fluoro-pyridin-2-yloxymethyl)-benzonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To an N,N-dimethylformamide (15 mL) solution of 2-chloro-4-fluoropyridine (2.88 g, 21.9 mmol) and 4-(hydroxymethyl)benzonitrile (4.37 g, 32.9 mmol) was added sodium hydride (1.29 g, 32.9 mmol, 60% in oil) at room temperature. This mixture was stirred for 4 hours at 70° C. This mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-2:1) to obtain the title compound (4.08 g, 82%).

Workup

  1. customThis mixture was partitioned into ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-2:1)

Sources & evidence

ORD record
ord-4c96f85b62814618ad72ee26180a6cff
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Linked notes

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