1-(2,4-dichlorophenyl)-2-(4-fluorophenyl)ethanone

反応条件: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of the ketone product from Step A (6.0 g; 21.3 mmol) in DMF (100 mL) in a dried round bottom flask was added N,N-dimethylformamide dimethyl acetal (11.3 mL; 85.1 mmol) under a N2 atmosphere, and the reaction was stirred at 75° C. for 16 hours. Most of the volatiles were removed in vacuo to afford the crude product as a oil which was used in the next step without further purification. Most of the volatiles were removed in vacuo

反応条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To an oven-dried three-neck round bottom flask fitted with a condenser and addition funnel flushed with N2 was added magnesium (4.23 g; 174 mmol) and anhydrous ether (100 mL). A solution of 4-flourobenzyl bromide (8.69 mL; 69.7 mmol) in ether (50 mL) was added dropwise via the addition funnel at room temperature. After the addition, the reaction mixture was heated at 40° C. for 2 hours. The reaction mixture was allowed to cool to room temperature and was cannulated into another dried flask charged with a solution of 2,4-dichlorobenzonitrile (10.0 g; 58.0 mmol) in ether (150 mL) under an N2 atmosphere. The resulting reaction mixture was stirred at 40° C. for 6 hours. The reaction was cooled to room temperature and quenched slowly with 2N aq. HCl, then partitioned between ethyl acetate and 2N aq. HCl. The organic portion was washed with 2N aq. HCl, water, brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was filtered through a silica gel plug (eluted with 20% ethyl acetate/hexane), and recrystallized from hexane to afford product: m/e=283 (M+1). To an oven-dried three-neck round bottom flask fitted with a condenser and addition funnel flushed with N2 After the addition to cool to room temperature was cannulated into another dried flask The resulting reaction mixture The reaction was cooled to room temperature quenched slowly with 2N aq. HCl partitioned between ethyl acetate and 2N aq. HCl The organic portion was washed with 2N aq. HCl, water, brine dried (Na2SO4) filtered concentrated in vacuo The crude product was filtered through a silica gel plug (eluted with 20% ethyl acetate/hexane) recrystallized from hexane to afford product

反応条件: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of the ketone product from Step A (6.0 g; 21.3 mmol) in DMF (100 mL) in a dried round bottom flask was added N,N-dimethylformamide dimethyl acetal (11.3 mL; 85.1 mmol) under a N2 atmosphere, and the reaction was stirred at 75° C. for 16 hours. Most of the volatiles were removed in vacuo to afford the crude product as a oil which was used in the next step without further purification. Most of the volatiles were removed in vacuo

反応条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To an oven-dried three-neck round bottom flask fitted with a condenser and addition funnel flushed with N2 was added magnesium (4.23 g; 174 mmol) and anhydrous ether (100 mL). A solution of 4-flourobenzyl bromide (8.69 mL; 69.7 mmol) in ether (50 mL) was added dropwise via the addition funnel at room temperature. After the addition, the reaction mixture was heated at 40° C. for 2 hours. The reaction mixture was allowed to cool to room temperature and was cannulated into another dried flask charged with a solution of 2,4-dichlorobenzonitrile (10.0 g; 58.0 mmol) in ether (150 mL) under an N2 atmosphere. The resulting reaction mixture was stirred at 40° C. for 6 hours. The reaction was cooled to room temperature and quenched slowly with 2N aq. HCl, then partitioned between ethyl acetate and 2N aq. HCl. The organic portion was washed with 2N aq. HCl, water, brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was filtered through a silica gel plug (eluted with 20% ethyl acetate/hexane), and recrystallized from hexane to afford product: m/e=283 (M+1). To an oven-dried three-neck round bottom flask fitted with a condenser and addition funnel flushed with N2 After the addition to cool to room temperature was cannulated into another dried flask The resulting reaction mixture The reaction was cooled to room temperature quenched slowly with 2N aq. HCl partitioned between ethyl acetate and 2N aq. HCl The organic portion was washed with 2N aq. HCl, water, brine dried (Na2SO4) filtered concentrated in vacuo The crude product was filtered through a silica gel plug (eluted with 20% ethyl acetate/hexane) recrystallized from hexane to afford product