Sodium hydride → 2-Fluoro-6-[1-(3-fluorophenyl)-ethoxy]-benzonitrile

HRID 2177008Notes

Reaction equation

HRID 2177008 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[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][CH:19]=[C:18]([O:10][CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[CH3:9])[C:15]=1[C:16]#[N:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 746952,6-DifluorobenzonitrileHCID 953483-Fluoro-alpha-methylbenzenemethanol

Product 1

HCID 247778992-Fluoro-6-[1-(3-fluorophenyl)-ethoxy]-benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 1-(3-fluorophenyl)ethanol (0.7 ml; 5.6 mmol) in dimethylformamide was added to a cooled (0° C.) slurry of sodium hydride (224 mg; 5.6 mmol) in dimethylformamide under nitrogen atmosphere. The reaction mixture was slowly warmed to room temperature, and stirred for 45 minutes. In another vessel, a solution of 2,6-difluorobenzonitrile (780 mg, 5.6 mmol) in dimethylformamide was chilled to 0° C., and activiated anion was added over 20 minutes. Mixture was then stirred 2 hours at room temperature. The reaction mixture was poured on crushed ice-water, stirred, filtered, washed with water and dried to afford g of solid (yield) of 2-fluoro-6-[1-(3-fluorophenyl)-ethoxy]-benzonitrile.

Workup

  1. additionactiviated anion was added over 20 minutes
  2. stirringMixture was then stirred 2 hours at room temperature
  3. additionThe reaction mixture was poured
  4. stirringstirred
  5. filtrationfiltered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-747cf355ff4c491783c9eaf7241a41c8
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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