279261-80-2

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:80.01; pressure:0.00; stir:

Procedure: In a 50 mL round-bottomed flask, PALLADIUM ACETATE (0.014 g, 0.06 mmol) was treated with BINAP (0.079 g, 0.13 mmol) under nitrogen in degassed Toluene (12.74 ml). The reaction was heated to 80 °C and was stirred for 10 min. To the flask was then added tert-butyl piperazine-1-carboxylate (0.237 g, 1.27 mmol), cesium carbonate (0.208 g, 0.64 mmol), potassium carbonate (0.176 g, 1.27 mmol), and 18-CROWN-6 (0.034 g, 0.13 mmol). The reaction was then treated with 4-bromo-2-chloro-1-ethoxybenzene (0.300 g, 1.27 mmol) and was allowed to stir at 80°C 5 h. **LCMS High pH:** No reaction observed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 4-bromo-2-chlorophenol (10.81 g) and potassium carbonate (8.65 g) in DMF (10 ml) was added at room temperature ethyl iodide (4.17 ml), and the mixture was stirred for 68 hours. To the mixture was added water, and the mixture was extracted with hexane. The organic layer was washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give pale yellow oil of 4-bromo-2-chloro-1-ethoxybenzene (12.28 g). the mixture was extracted with hexane The organic layer was washed with saturated brine dried with magnesium sulfate Under reduced pressure, the solvent was evaporated

Conditions: temp:80.01; pressure:0.00; stir: