1-(4-bromo-3-fluorophenyl)but-3-en-1-ol

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of the crude product from Step G (39.1 mmol) and Zn(CN)2 (4.59 g, 39.1 mmol) in 50 mL of DMF was degassed by bubbling argon through the mixture for 30 minutes. Tetrakis(triphenylphosphine)palladium (3.15 g, 2.73 mmol) was added, and the reaction was heated to 80° C. The solution was stirred over the course of 7 days, twice adding additional portions (2.0 mmol) of palladium catalyst. After cooling to room temperature, the solution was poured into EtOAc, washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by silica gel chromatography (10-15% EtOAc/hexane) provided the titled compound along with some of the aryl bromide starting material. by bubbling argon through the mixture for 30 minutes After cooling to room temperature washed with water and brine dried (Na2SO4) filtered concentrated in vacuo Purification by silica gel chromatography (10-15% EtOAc/hexane)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of the crude product from Step G (39.1 mmol) and Zn(CN)2 (4.59 g, 39.1 mmol) in 50 mL of DMF was degassed by bubbling argon through the mixture for 30 minutes. Tetrakis(triphenylphosphine)palladium (3.15 g, 2.73 mmol) was added, and the reaction was heated to 80° C. The solution was stirred over the course of 7 days, twice adding additional portions (2.0 mmol) of palladium catalyst. After cooling to room temperature, the solution was poured into EtOAc, washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by silica gel chromatography (10-15% EtOAc/hexane) provided the titled compound along with some of the aryl bromide starting material. by bubbling argon through the mixture for 30 minutes After cooling to room temperature washed with water and brine dried (Na2SO4) filtered concentrated in vacuo Purification by silica gel chromatography (10-15% EtOAc/hexane)

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

Procedure: To a solution of the aldehyde from Step F (7.97 g, 39.1 mmol) in 40 mL of THF at −78° C. under argon was added dropwise a solution of allymagnesium chloride in THF (23.4 mL, 46.9 mmol, 2M). After one hour, another portion of allymagnesium chloride solution was added (5 mL, 10 mmol). After an additional 30 minutes, the solution was quenched with saturated aqueous ammonium chloride, warmed to room temperature, and poured into ethyl acetate. The solution was washed with washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product. After an additional 30 minutes the solution was quenched with saturated aqueous ammonium chloride poured into ethyl acetate The solution was washed with washed with sat. aq. NaHCO3 and brine dried (Na2SO4) filtered concentrated in vacuo

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of the crude product from Step G (39.1 mmol) and Zn(CN)2 (4.59 g, 39.1 mmol) in 50 mL of DMF was degassed by bubbling argon through the mixture for 30 minutes. Tetrakis(triphenylphosphine)palladium (3.15 g, 2.73 mmol) was added, and the reaction was heated to 80° C. The solution was stirred over the course of 7 days, twice adding additional portions (2.0 mmol) of palladium catalyst. After cooling to room temperature, the solution was poured into EtOAc, washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by silica gel chromatography (10-15% EtOAc/hexane) provided the titled compound along with some of the aryl bromide starting material. by bubbling argon through the mixture for 30 minutes After cooling to room temperature washed with water and brine dried (Na2SO4) filtered concentrated in vacuo Purification by silica gel chromatography (10-15% EtOAc/hexane)

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

Procedure: To a solution of the aldehyde from Step F (7.97 g, 39.1 mmol) in 40 mL of THF at −78° C. under argon was added dropwise a solution of allymagnesium chloride in THF (23.4 mL, 46.9 mmol, 2M). After one hour, another portion of allymagnesium chloride solution was added (5 mL, 10 mmol). After an additional 30 minutes, the solution was quenched with saturated aqueous ammonium chloride, warmed to room temperature, and poured into ethyl acetate. The solution was washed with washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product. After an additional 30 minutes the solution was quenched with saturated aqueous ammonium chloride poured into ethyl acetate The solution was washed with washed with sat. aq. NaHCO3 and brine dried (Na2SO4) filtered concentrated in vacuo