1-bromo-4-(1-cyclopropylethoxy)benzene

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 0° C. slurry of NaH (460 mg, 11.4 mmol, 60 wt % dispersion in mineral oil) in DMF (14 mL) was added 1-cyclopropylethanol (0.79 mL, 7.41 mmol) dropwise. The cold bath was removed for 30 min before the addition of 1-bromo-4-fluorobenzene (1.00 g, 5.7 mmol). The resulting reaction mixture was heated to 100° C. for 3 h. At completion, the reaction was cooled to room temperature and concentrated. The resulting oil was diluted with water (30 mL) and extracted into EtOAc (3×30 mL). The combined organics were washed with brine (20 mL), then dried over MgSO4 and concentrated to provide 1-bromo-4-(1-cyclopropylethoxy)benzene (1.30 g, 95% yield). The resulting oil was used directly without further purification. The resulting reaction mixture At completion, the reaction was cooled to room temperature concentrated The resulting oil was diluted with water (30 mL) extracted into EtOAc (3×30 mL) The combined organics were washed with brine (20 mL) dried over MgSO4 concentrated