1-(3-chlorophenyl)-3-iodopropan-1-one

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(3-Chlorophenyl)-3-iodopropan-1-one: Intermediate 12A (2.415 g, 8.14 mmol) was dissolved in acetone (40.7 mL) and the above solution was cooled to 0° C. and Jones Reagent (6.08 ml, 16.29 mmol) was added dropwise. The reaction mixture turned orange/brown and was allowed to stir at 0° C. for 30 min. To the mixture was added 10 mL of isoproponal (reaction mixture turned green) and was then allowed to stir at rt for 10 min. The reaction mixture was then diluted with EtOAc and water. The organic layer was washed with water (3×) and brine, dried with magnesium sulfate, filtered and concentrated to yield a light yellow oil (which solidified into long yellow needles). The crude product was then purified using silica gel chromatography to yield the desired product as a white solid (2.16 g, 90%). MS (ESI) m/z: 294.8 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 7.93 (t, J=1.6 Hz, 1H), 7.85-7.81 (m, 1H), 7.59-7.56 (m, 1H), 7.47-7.42 (m, 1H), 3.65-3.60 (m, 2H), 3.49-3.43 (m, 2H) ppm. To the mixture was added 10 mL of isoproponal (reaction mixture turned green) to stir at rt for 10 min The organic layer was washed with water (3×) and brine dried with magnesium sulfate filtered concentrated to yield a light yellow oil (which The crude product was then purified

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(3-Chlorophenyl)-3-iodopropan-1-one: Intermediate 12A (2.415 g, 8.14 mmol) was dissolved in acetone (40.7 mL) and the above solution was cooled to 0° C. and Jones Reagent (6.08 ml, 16.29 mmol) was added dropwise. The reaction mixture turned orange/brown and was allowed to stir at 0° C. for 30 min. To the mixture was added 10 mL of isoproponal (reaction mixture turned green) and was then allowed to stir at rt for 10 min. The reaction mixture was then diluted with EtOAc and water. The organic layer was washed with water (3×) and brine, dried with magnesium sulfate, filtered and concentrated to yield a light yellow oil (which solidified into long yellow needles). The crude product was then purified using silica gel chromatography to yield the desired product as a white solid (2.16 g, 90%). MS (ESI) m/z: 294.8 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 7.93 (t, J=1.6 Hz, 1H), 7.85-7.81 (m, 1H), 7.59-7.56 (m, 1H), 7.47-7.42 (m, 1H), 3.65-3.60 (m, 2H), 3.49-3.43 (m, 2H) ppm. To the mixture was added 10 mL of isoproponal (reaction mixture turned green) to stir at rt for 10 min The organic layer was washed with water (3×) and brine dried with magnesium sulfate filtered concentrated to yield a light yellow oil (which The crude product was then purified