Sodium hydride → 2-Fluoro-6-(3-iodobenzyloxy)-benzonitrile

HRID 2176998Notes

Reaction equation

HRID 2176998 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][OH:8].[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17](F)[C:14]=1[C:15]#[N:16]>CN(C=O)C>[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([O:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([I:3])[CH:5]=2)[C:14]=1[C:15]#[N:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 423003-Iodobenzyl alcoholHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 669243542-Fluoro-6-(3-iodobenzyloxy)-benzonitrileYield 73.2%

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 3-iodobenzyl alcohol (1.85 g; 7.9 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 refrigerated overnight. The resulting solid is filtered, washed with water, and dried under vacuum at 30° C. overnight to give 1.86 grams of 2-fluoro-6-(3-iodobenzyloxy)-benzonitrile.

Workup

  1. waitallowed to room temperature over 2 hours
  2. filtrationThe resulting solid is filtered
  3. washwashed with water
  4. customdried under vacuum at 30° C. overnight

Sources & evidence

ORD record
ord-a8e5776db97449fbbd2c334675dc20f5
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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