Sodium hydride → 2-[1-(3,4-Dichlorophenyl)-ethoxy]-6-fluorobenzonitrile

HRID 2176999Notes

Reaction equation

HRID 2176999 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([OH:13])[CH3:12])[CH:7]=[CH:8][C:9]=1[Cl:10].[F:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19](F)[C:16]=1[C:17]#[N:18]>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([O:13][C:19]2[CH:20]=[CH:21][CH:22]=[C:15]([F:14])[C:16]=2[C:17]#[N:18])[CH3:12])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 746952,6-DifluorobenzonitrileHCID 978993,4-Dichloro-alpha-methylbenzenemethanol

Product 1

HCID 247775482-[1-(3,4-Dichlorophenyl)-ethoxy]-6-fluorobenzonitrileYield 86.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a cold (ice water) suspension of sodium hydride (316 mg; 7.9 mmol) in anhydrous DMF (10 mL) is added a solution of 1-(3,4-dichlorophenyl)-ethanol (1.40 g; 7.3 mmol) in anhydrous DMF (5 mL) over 30 minutes. After allowing to room temperature over 30 minutes, this solution is added to a cold (ice water) stirred solution of 2,6-difluorobenzonitrile (1.0 g; 7.2 mmol) in anhydrous DMF (15 mL), and allowed to room temperature over 2 hours. The reaction mixture is poured into ice water with vigorous stirring and extracted with ethyl acetate. The organics are separated and dried over magnesium sulfate. The solvent is removed and the resulting oil is dried under vacuum at 30° C. overnight to give 1.93 gm of 2-[1-(3,4-dichlorophenyl)-ethoxy]-6-fluorobenzonitrile.

Workup

  1. waitallowed to room temperature over 2 hours
  2. extractionextracted with ethyl acetate
  3. customThe organics are separated
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is removed
  6. customthe resulting oil is dried under vacuum at 30° C. overnight

Sources & evidence

ORD record
ord-b74ee71167484535b63235aaaae79380
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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