Sodium hydride → HCID 54970853, compound

HRID 1364403Notes

Reaction equation

HRID 1364403 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1.[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>[Br:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][O:9][C:17]2[CH:18]=[CH:19][CH:20]=[C:13]([F:12])[C:14]=2[C:15]#[N:16])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 701194-Bromobenzyl alcoholHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 54970853HCID 54970853, compoundYield 82.6%

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 4-bromobenzyl alcohol (1.48 g; 7.9 mmol) in anhydrous DMF (5 mL) over 10 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 g; 7.2 mmol) in anhydrous DMF (15 mL), and allowed to room temperature over 3 hours. The reaction mixture is poured into ice water with vigorous stirring and refrigerated overnight. The resulting precipitate is removed by filtration and dried under vacuum at 30° C. overnight to give 1.82 grams 2-(4-bromobenzyloxy)-6-fluorobenzonitrile.

Workup

  1. waitallowed to room temperature over 3 hours
  2. customThe resulting precipitate is removed by filtration
  3. customdried under vacuum at 30° C. overnight

Sources & evidence

ORD record
ord-2206b20412184f8e87542fd7c438578a
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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