Veratryl alcohol → HCID 66924131, compound

HRID 1364406Notes

Reaction equation

HRID 1364406 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH2:8][OH:9].[F:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20](F)[C:17]=1[C:18]#[N:19]>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH2:8][O:9][C:20]1[CH:21]=[CH:22][CH:23]=[C:16]([F:15])[C:17]=1[C:18]#[N:19]

Participants

5

Reactant 3

HCID 7118Veratryl alcoholHCID 24758Sodium hydrideHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 66924131HCID 66924131, compoundYield 87.5%

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 3,4-dimethoxybenzyl alcohol (1.33 gm; 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 overnight at 30° C. to give 1.81 grams of 2-(3,4-dimethoxybenzyloxy)-6-fluorobenzonitrile.

Workup

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

Sources & evidence

ORD record
ord-074b9802e9ba48c0a082a30b75e7ba73
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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