Sodium hydride → HCID 18525684, compound

HRID 1364430Notes

Reaction equation

HRID 1364430 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[H-].[Na+].[F:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20](F)[C:17]=1[C:18]#[N:19]>CN(C)C=O>[F:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([O:8][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([C:2]([F:11])([F:12])[F:1])=[CH:4][CH:5]=2)[C:17]=1[C:18]#[N:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 676844-(Trifluoromethyl)benzenemethanolHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 18525684HCID 18525684, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(Trifluoromethyl)benzyl alcohol (1.15 g; 6.3 mmol) was added to a cooled (0° C.) slurry of sodium hydride (249.7 mg; 6.2 mmol) in dimethylformamide under nitrogen atmosphere. The reaction mixture was slowly warmed to room temperature overnight. The reaction mixture was then added to a cooled (0° C.) solution of 2,6-difluorobenzonitrile in dimethylfomamide, stirred for 6 hours at room temperature. The reaction mixture was poured on crushed ice-water, stirred, filtered, washed with water and dried to afford 804.4 milligrams of 2-fluoro-6-(4-trifluoromethylphenylmethoxy)-benzonitrile as waxy yellow solid. Yield 45%.

Workup

  1. additionThe reaction mixture was then added to
  2. additionThe reaction mixture was poured
  3. stirringstirred
  4. filtrationfiltered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-3b786a8a86d143e099026749d34c6614
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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