Sodium hydride → HCID 66924362, compound

HRID 1364477Notes

Reaction equation

HRID 1364477 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H: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][C:19]([O:10][C@H:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH3:9])=[CH:18][C:15]=1[C:16]#[N:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 746952,6-DifluorobenzonitrileHCID 6950741(1S)-1-(3-CHLOROPHENYL)ETHANOL

Product 1

HCID 66924362HCID 66924362, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of (S)-1-(3-chlorophenyl)ethanol (20.4 g, 130.26 mmol) in dimethylformamide was added to a cooled (0° C.) slurry of sodium hydride (5.73 g, 143.29 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 (19.93 g, 143.29 mmol) in dimethylfomamide was added, stirred overnight at room temperature. The reaction mixture was poured on crushed ice-water, stirred, extracted with ether, dried, filtered and concentrated to afford 30.0 g of 2-fluoro-5-[(S)-1-(3-chlorophenyl)ethoxy]benzonitrile.

Workup

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

Sources & evidence

ORD record
ord-851ddc7915b341509a3178493ca92cff
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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