6-bromo-4,4-dimethyl-8-propan-2-yl-2,3-dihydrochromene

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

Procedure: 6-Bromo-4,4-dimethyl-8-(propan-2-yl)-3,4-dihydro-2H-chromene (154 mg, 0.54 mmol) in tetrahydrofuran (5.44 mL) was cooled to −78° C. and n-BuLi (261 μL, 0.65 mmol) was added dropwise via a syringe. The reaction mixture was stirred at −78° C. for 30 minutes, and then DMF (168 μL, 2.17 mmol) was added dropwise. The resulting mixture was allowed to warm to room temperature, and stirred for 30 minutes before water was added. It was then extracted with EtOAc (2×) and the combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum. The crude residue was purified by silica gel chromatography eluting with 0-10% EtOAc/Hexanes to obtain the desired product as a colorless oil. to warm to room temperature was added It was then extracted with EtOAc (2×) the combined organic layers were dried over Na2SO4 filtered concentrated under vacuum The crude residue was purified by silica gel chromatography eluting with 0-10% EtOAc/Hexanes

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

Procedure: 4-Bromo-1-[(3-methylbut-3-en-1-yl)oxy]-2-(propan-2-yl)benzene (293 mg, 1.03 mmol) dissolved in dichloromethane (3.10 mL) was cooled to 0° C. and aluminum chloride (138 mg, 1.03 mmol) in dichloromethane (3.0 mL) was added via a syringe. The reaction mixture was stirred at 0° C. for 30 minutes. It was then poured into an Erlenmeyer flask containing a 10% aqueous NaOH solution and ice. The mixture was extracted with dichloromethane (2×), and the combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum. The crude residue was purified by silica gel chromatography, eluting with 0-10% EtOAc/Hexanes to give the title compound as a colorless oil. It was then poured into an Erlenmeyer flask The mixture was extracted with dichloromethane (2×) the combined organic layers were dried over Na2SO4 filtered concentrated under vacuum The crude residue was purified by silica gel chromatography eluting with 0-10% EtOAc/Hexanes

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

Procedure: 6-Bromo-4,4-dimethyl-8-(propan-2-yl)-3,4-dihydro-2H-chromene (154 mg, 0.54 mmol) in tetrahydrofuran (5.44 mL) was cooled to −78° C. and n-BuLi (261 μL, 0.65 mmol) was added dropwise via a syringe. The reaction mixture was stirred at −78° C. for 30 minutes, and then DMF (168 μL, 2.17 mmol) was added dropwise. The resulting mixture was allowed to warm to room temperature, and stirred for 30 minutes before water was added. It was then extracted with EtOAc (2×) and the combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum. The crude residue was purified by silica gel chromatography eluting with 0-10% EtOAc/Hexanes to obtain the desired product as a colorless oil. to warm to room temperature was added It was then extracted with EtOAc (2×) the combined organic layers were dried over Na2SO4 filtered concentrated under vacuum The crude residue was purified by silica gel chromatography eluting with 0-10% EtOAc/Hexanes

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

Procedure: 4-Bromo-1-[(3-methylbut-3-en-1-yl)oxy]-2-(propan-2-yl)benzene (293 mg, 1.03 mmol) dissolved in dichloromethane (3.10 mL) was cooled to 0° C. and aluminum chloride (138 mg, 1.03 mmol) in dichloromethane (3.0 mL) was added via a syringe. The reaction mixture was stirred at 0° C. for 30 minutes. It was then poured into an Erlenmeyer flask containing a 10% aqueous NaOH solution and ice. The mixture was extracted with dichloromethane (2×), and the combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum. The crude residue was purified by silica gel chromatography, eluting with 0-10% EtOAc/Hexanes to give the title compound as a colorless oil. It was then poured into an Erlenmeyer flask The mixture was extracted with dichloromethane (2×) the combined organic layers were dried over Na2SO4 filtered concentrated under vacuum The crude residue was purified by silica gel chromatography eluting with 0-10% EtOAc/Hexanes

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

Procedure: 6-Bromo-4,4-dimethyl-8-(propan-2-yl)-3,4-dihydro-2H-chromene (154 mg, 0.54 mmol) in tetrahydrofuran (5.44 mL) was cooled to −78° C. and n-BuLi (261 μL, 0.65 mmol) was added dropwise via a syringe. The reaction mixture was stirred at −78° C. for 30 minutes, and then DMF (168 μL, 2.17 mmol) was added dropwise. The resulting mixture was allowed to warm to room temperature, and stirred for 30 minutes before water was added. It was then extracted with EtOAc (2×) and the combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum. The crude residue was purified by silica gel chromatography eluting with 0-10% EtOAc/Hexanes to obtain the desired product as a colorless oil. to warm to room temperature was added It was then extracted with EtOAc (2×) the combined organic layers were dried over Na2SO4 filtered concentrated under vacuum The crude residue was purified by silica gel chromatography eluting with 0-10% EtOAc/Hexanes

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

Procedure: 4-Bromo-1-[(3-methylbut-3-en-1-yl)oxy]-2-(propan-2-yl)benzene (293 mg, 1.03 mmol) dissolved in dichloromethane (3.10 mL) was cooled to 0° C. and aluminum chloride (138 mg, 1.03 mmol) in dichloromethane (3.0 mL) was added via a syringe. The reaction mixture was stirred at 0° C. for 30 minutes. It was then poured into an Erlenmeyer flask containing a 10% aqueous NaOH solution and ice. The mixture was extracted with dichloromethane (2×), and the combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum. The crude residue was purified by silica gel chromatography, eluting with 0-10% EtOAc/Hexanes to give the title compound as a colorless oil. It was then poured into an Erlenmeyer flask The mixture was extracted with dichloromethane (2×) the combined organic layers were dried over Na2SO4 filtered concentrated under vacuum The crude residue was purified by silica gel chromatography eluting with 0-10% EtOAc/Hexanes