1-bromo-2-(2,2-dimethylpropoxy)benzene

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A vial was charged with 1-bromo-2-iodobenzene (627 μL, 5 mmol), neopentyl alcohol (4.85 g, 55.0 mmol), copper(I) iodide (95 mg, 0.500 mmol), 1,10-phenanthroline (180 mg, 1.000 mmol) and cesium carbonate (2.28 g, 7.00 mmol). The vial was sealed under air atmosphere and heated to 100° C. for 12 h. The reaction mixture was cooled to RT and filtered through a pad of silica gel. The silica gel was washed with Et2O. The filtrate was concentrated and the residue was purified by column chromatography (100% hexanes) to yield the 1-bromo-2-(neopentyloxy)benzene as a colorless oil. The vial was sealed under air atmosphere The reaction mixture was cooled to RT filtered through a pad of silica gel The silica gel was washed with Et2O The filtrate was concentrated the residue was purified by column chromatography (100% hexanes)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A vial was charged with 1-bromo-2-iodobenzene (627 μL, 5 mmol), neopentyl alcohol (4.85 g, 55.0 mmol), copper(I) iodide (95 mg, 0.500 mmol), 1,10-phenanthroline (180 mg, 1.000 mmol) and cesium carbonate (2.28 g, 7.00 mmol). The vial was sealed under air atmosphere and heated to 100° C. for 12 h. The reaction mixture was cooled to RT and filtered through a pad of silica gel. The silica gel was washed with Et2O. The filtrate was concentrated and the residue was purified by column chromatography (100% hexanes) to yield the 1-bromo-2-(neopentyloxy)benzene as a colorless oil. The vial was sealed under air atmosphere The reaction mixture was cooled to RT filtered through a pad of silica gel The silica gel was washed with Et2O The filtrate was concentrated the residue was purified by column chromatography (100% hexanes)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A vial was charged with 1-bromo-2-iodobenzene (627 μL, 5 mmol), neopentyl alcohol (4.85 g, 55.0 mmol), copper(I) iodide (95 mg, 0.500 mmol), 1,10-phenanthroline (180 mg, 1.000 mmol) and cesium carbonate (2.28 g, 7.00 mmol). The vial was sealed under air atmosphere and heated to 100° C. for 12 h. The reaction mixture was cooled to RT and filtered through a pad of silica gel. The silica gel was washed with Et2O. The filtrate was concentrated and the residue was purified by column chromatography (100% hexanes) to yield the 1-bromo-2-(neopentyloxy)benzene as a colorless oil. The vial was sealed under air atmosphere The reaction mixture was cooled to RT filtered through a pad of silica gel The silica gel was washed with Et2O The filtrate was concentrated the residue was purified by column chromatography (100% hexanes)