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

HRID 2176996Notes

Reaction equation

HRID 2176996 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7].[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:7][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[I:3])[C:14]=1[C:15]#[N:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 746952,6-DifluorobenzonitrileHCID 1076292-Iodobenzylic alcohol

Product 1

HCID 669243012-Fluoro-6-(2-iodobenzyloxy)-benzonitrileYield 79.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a cold (ice water) suspension of sodium hydride (216 mg; 5.0 mmol) in anhydrous DMF (4 mL) is added a solution of 2-iodobenzyl alcohol (1.17 gm; 5.0 mmol) in anhydrous DMF (5 mL) over 10 minutes. After allowing to room temperature over 45 minutes, this solution is added to a cold (ice water) stirred solution of 2,6-difluorobenzonitrile (702 mg; 5.0 mmol) in anhydrous DMF (3 mL), and allowed to room temperature over 4 hours. The reaction mixture is poured into ice water with vigorous stirring and the resulting solid is filtered, washed with water, and dried under vacuum at 40° C. for 3 hours to give 1.40 grams of 2-fluoro-6-(2-iodobenzyloxy)-benzonitrile.

Workup

  1. waitallowed to room temperature over 4 hours
  2. filtrationthe resulting solid is filtered
  3. washwashed with water
  4. customdried under vacuum at 40° C. for 3 hours

Sources & evidence

ORD record
ord-870c94f2c8404c579ca77571f1a69f9b
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

Loading…