Cesium carbonate → HCID 68982994, compound

Participants

Reaction Steps

A mixture of 1-bromo-6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthol (351 mg, 0.918 mmol), prepared in step 1 of Example 3, bromoacetonitrile (77 μL, 1.11 mmol) and cesium carbonate (1.505 g, 4.62 mmol) in 25 mL of acetone was stirred under nitrogen at room temperature for 19 h (overnight). The reaction was concentrated under reduced pressure to remove the acetone. The residue was partitioned between methylene chloride and water. The aqueous layer was separated and extracted three times with methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give {[1-bromo-6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}acetonitrile (382 mg, 99%) as a light tan solid, mp 157-160° C. Elemental Analysis for C21H13BrN2OS Calc'd: C, 59.87; H, 3.11; N, 6.65. Found: C, 59.56; H, 3.28; N, 6.56.

Provenance & Evidence