Potassium Carbonate → ({4-[(4-Fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene) methyl]phenyl}oxy)acetonitrile

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Reaction Steps

The o-alkylation procedure described for 10 (example 5, step 2) was employed. To a stirred suspension of 4-[(4-fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene) methyl]phenol 9 (0.508 g, 1.5 mmol), K2CO3 (0.414 g, 3.0 mmol), and acetone (50 mL) was added, under N2 at RT, bromoacetonitrile (0.21 mL, 3.0 mmol). The reaction mixture was refluxed for 4 h, cooled to RT, and filtered. Standard work-up followed by purification afforded 0.410 g (72%) of the title compound 14 as a white foam. mp 100-101° C. 1H NMR (300 MHz, CDCl3): δ 7.18-7.11 (m, 4H), 6.99 and 6.97 (dd, J1=8.7 Hz, J2=8.7 Hz, 2H), 6.92 (d, J=8.7 Hz, 2H), 4.76 (s, 2H), 1.98 (s, 2H), 1.97 (s, 2H), 1.32 (s, 2H), 0.96 (s, 12H). LCMS (ESI): m/z 376 (M−H)−. Anal. Calcd for C25H28FNO, C, 79.54, H, 7.48; N, 3.71. Found: C, 79.21, H, 7.46; N, 3.73.

Provenance & Evidence