Sodium hydride → HCID 66924074, compound

HRID 2176972Notes

Reaction equation

HRID 2176972 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][OH:7])=[CH:2]1.[H-].[Na+].[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15](F)[C:12]=1[C:13]#[N:14]>CN(C)C=O>[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([O:7][CH2:6][C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[C:12]=1[C:13]#[N:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 746952,6-DifluorobenzonitrileHCID 123570Thiophene-3-methanol

Product 1

HCID 66924074HCID 66924074, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-thiophenemethanol (1.0 g; 8.76 mmol) in dimethylformamide was added to a cooled (0° C.) slurry of sodium hydride (0.42 g; 10.51 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 in dimethylfomamide was added, stirred overnight at room temperature. The reaction mixture was poured on crushed ice-water, stirred, filtered, washed with water and dried to afford 600 milligrams of 2-fluoro-6-(thiophen-3-ylmethoxy)benzonitrile.

Workup

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

Sources & evidence

ORD record
ord-20c809fb84b54f9c8fe1237e0dfc4670
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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