2-bromo-1-chloro-4-propan-2-ylbenzene

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-bromo-1-chloro-4-isopropylbenzene (0.37 g, 1-59 mmol) in dry THF (5 mL) at −78° C., n-butyl lithium (0.76 mL, 1.90 mmol, 2.5 M) was added. The solution was stirred at −78° C. for 30 min. Trimethyl borate (0.53 mL, 4.76 mmol) was added. The solution was stirred at −78° C. for 2.5 h. The reaction was quenched with saturated aqueous NH4Cl. The aqueous layer was extracted with EtOAc (3×15 mL). The combined EtOAc layers were dried over Na2SO4. The residue was used without further purification after evaporation of the solvent. The solution was stirred at −78° C. for 2.5 h The reaction was quenched with saturated aqueous NH4Cl The aqueous layer was extracted with EtOAc (3×15 mL) The combined EtOAc layers were dried over Na2SO4 The residue was used without further purification after evaporation of the solvent

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-bromo-1-chloro-4-isopropylbenzene (0.37 g, 1-59 mmol) in dry THF (5 mL) at −78° C., n-butyl lithium (0.76 mL, 1.90 mmol, 2.5 M) was added. The solution was stirred at −78° C. for 30 min. Trimethyl borate (0.53 mL, 4.76 mmol) was added. The solution was stirred at −78° C. for 2.5 h. The reaction was quenched with saturated aqueous NH4Cl. The aqueous layer was extracted with EtOAc (3×15 mL). The combined EtOAc layers were dried over Na2SO4. The residue was used without further purification after evaporation of the solvent. The solution was stirred at −78° C. for 2.5 h The reaction was quenched with saturated aqueous NH4Cl The aqueous layer was extracted with EtOAc (3×15 mL) The combined EtOAc layers were dried over Na2SO4 The residue was used without further purification after evaporation of the solvent

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

Procedure: Add bis(dibenzylideneacetone)palladium (49.2 mg, 85.6 μmol) to a round bottom flask and seal with a septum. Flush with nitrogen. Add tri-tert-butylphosphine (85.6 μL, 85.6 μmol, 1M in toluene) and lithium bis(trimethylsilyl)amide (12.8 mL, 11.56 mmol, 0.9M in methylcyclohexanes) via a syringe. Add 2-bromo-1-chloro-4-isopropyl-benzene (1.0 g, 4.28 mmol) and t-butyl acetate (865.2 μL, 6.42 mmol) via a syringe. Add toluene (10.7 mL) via a syringe and the reaction mixture becomes hot to the touch. Place on an ambient temperature water bath and stir for 3 hours. Store the reaction mixture in the freezer over the weekend. Warm the reaction mixture to ambient temperature. Dilute the reaction mixture with diethyl ether and add saturated ammonium chloride solution. Separate the layers and wash the diethyl ether layer with saturated sodium chloride solution. Dry over sodium sulfate, filter and concentrate under reduced pressure. Purify the residue by silica gel chromatography eluting with acetone: hexanes (0-2% gradient) to give the title compound (1.04 g). Purify again by silica gel chromatography eluting with dichloromethane: hexanes (0-20% gradient) to give the title compound (490 mg, 1.82 mmol). MS (m/z): 213.0 (M-tBu+1). seal with a septum Flush with nitrogen Place on an ambient temperature Separate the layers wash the diethyl ether layer with saturated sodium chloride solution Dry over sodium sulfate filter concentrate under reduced pressure Purify the residue by silica gel chromatography eluting with acetone

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-bromo-1-chloro-4-isopropylbenzene (0.37 g, 1-59 mmol) in dry THF (5 mL) at −78° C., n-butyl lithium (0.76 mL, 1.90 mmol, 2.5 M) was added. The solution was stirred at −78° C. for 30 min. Trimethyl borate (0.53 mL, 4.76 mmol) was added. The solution was stirred at −78° C. for 2.5 h. The reaction was quenched with saturated aqueous NH4Cl. The aqueous layer was extracted with EtOAc (3×15 mL). The combined EtOAc layers were dried over Na2SO4. The residue was used without further purification after evaporation of the solvent. The solution was stirred at −78° C. for 2.5 h The reaction was quenched with saturated aqueous NH4Cl The aqueous layer was extracted with EtOAc (3×15 mL) The combined EtOAc layers were dried over Na2SO4 The residue was used without further purification after evaporation of the solvent