Iodoethane → 4-Acetyl-2-bromo-6-chloro-3-ethoxybenzonitrile

Participants

Reaction Conditions

Reaction Steps

The 1-(3-bromo-5-chloro-4-fluoro-2-hydroxyphenyl)ethanone (3.0 g, 11 mmol, from Example 187, Step 2) was dissolved in DMF (24 mL) and potassium cyanide (0.88 g, 13 mmol) was added. The reaction was heated to 85° C. and monitored by LC/MS. After heating for 18 h the reaction was complete. The reaction was allowed to cool to room temperature and then potassium carbonate (3.1 g, 22 mmol) and iodoethane (1.3 mL, 17 mmol) were added. The reaction was heated to 60° C. overnight. After stirring for 18 h the reaction was complete. The crude was diluted with EtOAc and washed with water, brine, dried over magnesium sulfate and concentrated to give the crude product as a dark oil. The product was purified by chromatography on silica gel eluting with hexane:EtOAc gradient to give 4-acetyl-2-bromo-6-chloro-3-ethoxybenzonitrile as an oil which solidified (2.1 g, 62%). LCMS calculated for C11H10BrClNO2(M+H)+: m/z=301.9, 303.9. found: 301.6, 303.6.

Provenance & Evidence