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0 °C

In an 18 mL vial, sodium hydride was suspended in 2 mL dry dimethylformamide and chilled to 0° C. under nitrogen flow. 4-(2-Fluorobenzyl)cyclohexylmethanol (155 mg; 0.7 mmol) was added over 2 minutes and warmed to room temperature for 2 hours. Mixture was then added to a 0° C. mixture of 2,6-difluorobenzonitrile (97 mg; 0.7 mmol) in 2 mL of dimethylformamide over 1 minute and mixture continued to stir an additional 2 hours. Mixture was quenched over 10 g of ice and extracted 3× ethyl acetate 20 mL each. Combined organics were washed 5× water, brine and dried over MgSO4. Colorless oil was obtained and purified by flash chromatography (20:1) with 0-5% ethyl acetate in hexanes to give 233 mg of title compound. (98% yield).

1. temperaturewarmed to room temperature for 2 hours
2. additionMixture was then added to a 0° C.
3. customMixture was quenched over 10 g of ice
4. extractionextracted 3× ethyl acetate 20 mL each
5. washCombined organics were washed 5× water, brine
6. dry with materialdried over MgSO4
7. customColorless oil was obtained
8. custompurified by flash chromatography (20:1) with 0-5% ethyl acetate in hexanes