Sodium hydride → HCID 66924353, compound

Participants

Reaction Steps

To a cold (ice water) suspension of sodium hydride (206 mg; 5.0 mmol) in anhydrous DMF (4 mL) is added a solution of 1-adamantane methanol (830 mg; 4.9 mmol) in anhydrous DMF (5 mL) over 10 minutes. After allowing to room temperature over 40 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 3 hours. The reaction mixture is poured into ice water with vigorous stirring and extracted with ethyl acetate. The organics are separated and dried over magnesium sulfate. The solvent is removed and the resulting solid is dried under vacuum at 40° C. for 3 hours to give 1.32 grams of 2-(adamantan-1-ylmethoxy)-6-fluorobenzonitrile.

Provenance & Evidence