1-(4-bromophenyl)butan-2-one

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of 70B (478 mg, 2.1 mmol) in 5 mL MeOH at 0° C., was added NaBH4 (110 mg, 2.98 mmol). The solution was stirred at rt for 30 min, then was diluted with EtOAc and washed with H2O and brine, dried (Na2SO4) and concentrated. Purification via flash chromatography (0-30% EtOAc/hexanes) afforded 70C (460 mg, 96%). MS (ESI) m/z 221.2 (M-OH)+. washed with H2O and brine dried (Na2SO4) concentrated Purification via flash chromatography (0-30% EtOAc/hexanes)

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

Procedure: To a solution of 70B (478 mg, 2.1 mmol) in 5 mL MeOH at 0° C., was added NaBH4 (110 mg, 2.98 mmol). The solution was stirred at rt for 30 min, then was diluted with EtOAc and washed with H2O and brine, dried (Na2SO4) and concentrated. Purification via flash chromatography (0-30% EtOAc/hexanes) afforded 70C (460 mg, 96%). MS (ESI) m/z 221.2 (M-OH)+. washed with H2O and brine dried (Na2SO4) concentrated Purification via flash chromatography (0-30% EtOAc/hexanes)

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

Procedure: To a round bottom flask contained EtMgCl (10 mL, 2M in THF, 20 mmol) at 0° C., was added a solution of 70A (516 mg, 2 mmol) in 10 mL THF. The solution was stirred at rt for 30 min, then was quenched with sat. NH4Cl and extracted with EtOAc (3×20 mL). The organic layer washed with brine, dried (Na2SO4) and concentrated. Purification via flash chromatography (0-30% EtOAc/hexanes) afforded 70B (288 mg, 65%). MS (ESI) m/z 227.1 (M+H)+. To a round bottom flask contained was quenched with sat. NH4Cl extracted with EtOAc (3×20 mL) The organic layer washed with brine dried (Na2SO4) concentrated Purification via flash chromatography (0-30% EtOAc/hexanes)

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of 70B (478 mg, 2.1 mmol) in 5 mL MeOH at 0° C., was added NaBH4 (110 mg, 2.98 mmol). The solution was stirred at rt for 30 min, then was diluted with EtOAc and washed with H2O and brine, dried (Na2SO4) and concentrated. Purification via flash chromatography (0-30% EtOAc/hexanes) afforded 70C (460 mg, 96%). MS (ESI) m/z 221.2 (M-OH)+. washed with H2O and brine dried (Na2SO4) concentrated Purification via flash chromatography (0-30% EtOAc/hexanes)

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

Procedure: To a round bottom flask contained EtMgCl (10 mL, 2M in THF, 20 mmol) at 0° C., was added a solution of 70A (516 mg, 2 mmol) in 10 mL THF. The solution was stirred at rt for 30 min, then was quenched with sat. NH4Cl and extracted with EtOAc (3×20 mL). The organic layer washed with brine, dried (Na2SO4) and concentrated. Purification via flash chromatography (0-30% EtOAc/hexanes) afforded 70B (288 mg, 65%). MS (ESI) m/z 227.1 (M+H)+. To a round bottom flask contained was quenched with sat. NH4Cl extracted with EtOAc (3×20 mL) The organic layer washed with brine dried (Na2SO4) concentrated Purification via flash chromatography (0-30% EtOAc/hexanes)