1-bromo-4-(3-phenylpropyl)benzene

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-bromo-4-(3-phenylpropyl)-benzene (684 mg, 2.48 mmol) in DMF (10 mL) were added acrolein diethyl acetal (1.7 mL, 11.1 mmol), tetrabutylammonium acetate (1.87 g, 6.2 mmol), potassium carbonate (514 mg, 3.72 mmol), potassium chloride (185 mg, 2.48 mmol), and palladium(II) acetate (50 mg, 0.22 mmol). After stirring at 90° C. for 4 h, the reaction mixture was cooled to RT and HCl (2M, 15 mL) was added. After stirring for 10 min at RT, the mixture was extracted with MTBE and washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. Purification by MPLC (20% ethyl acetate in hexanes) gave 390 mg (2E)-3-[4-(3-phenylpropyl)phenyl]acrylaldehyde as a yellow oil. the reaction mixture was cooled to RT After stirring for 10 min at RT the mixture was extracted with MTBE washed with water and brine dried over MgSO4 concentrated under reduced pressure Purification by MPLC (20% ethyl acetate in hexanes)