Sodium hydride → HCID 66924299, compound

HRID 1364450Notes

Reaction equation

HRID 1364450 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][OH:6].[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:6][CH2:5][C:4]2[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=2[O:2][CH3:1])=[CH:18][C:15]=1[C:16]#[N:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 691542-Methoxybenzyl alcoholHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 66924299HCID 66924299, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-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 1.55 g of 2-fluoro-5-(2-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-80ef2109ba9e46f3af450567e02b9964
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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