Sodium hydride → HCID 66924202, compound

HRID 1364451Notes

Reaction equation

HRID 1364451 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][OH:7].[H-].[Na+].[F:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:18](F)[C:15]=1[C:16]#[N:17]>CN(C)C=O>[F:13][C:14]1[CH:21]=[CH:20][C:19]([O:7][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:18][C:15]=1[C:16]#[N:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 746952,6-DifluorobenzonitrileHCID 814373-Methoxybenzyl alcohol

Product 1

HCID 66924202HCID 66924202, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-methoxybenzyl alcohol (1.0 g, 7.2 mmol) in dimethylformamide was added to a cooled (0° C.) slurry of sodium hydride (0.32 g, 7.91 mmol) in dimethylformamide under nitrogen atmosphere. The reaction mixture was slowly warmed to room temperature, stirred for 1 hour. Again, cooled (0° C.), then a solution of 2,6-difluorobenzonitrile (1.0 g, 7.2 mmol) in dimethylfomamide was added, stirred overnight at room temperature. The reaction mixture was poured on crushed ice-water, stirred, filtered and dried to afford 1.6 g of 2-fluoro-5-(3-methoxybenzyloxy)benzonitrile.

Workup

  1. temperatureAgain, cooled (0° C.)
  2. stirringstirred overnight at room temperature
  3. additionThe reaction mixture was poured
  4. stirringstirred
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-b34877f80dfd4f14884ba5b4f37cedae
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

Loading…