Sodium hydride → HCID 54970807, compound

HRID 1364415Notes

Reaction equation

HRID 1364415 reaction equation
[H-].[Na+].[Br: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[Br:3])[C:14]=1[C:15]#[N:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 728502-Bromobenzyl alcoholHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 54970807HCID 54970807, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a cold (ice water) suspension of sodium hydride (222 mg; 5.0 mmol) in anhydrous DMF (4 mL) is added a solution of 2-bromobenzyl alcohol (941 mg; 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 (703 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 1.27 grams of 2-fluoro-6-(2-bromobenzyloxy)-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-3ec4072a62fb40449fb3f6a5d47f9ef0
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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