2-bromo-1-(2,2-dimethylpropoxy)-3-methylbenzene

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A vial was charged with 2-bromo-1-iodo-3-methylbenzene (677 mg, 2.28 mmol), neopentyl alcohol (2.21 g, 25.08 mmol), copper(I) iodide (43.4 mg, 0.228 mmol), 1,10-phenanthroline (82 mg, 0.456 mmol) and cesium carbonate (1.04 mg, 3.19 mmol). The vial was sealed under air atmosphere and heated to 110° C. for 24 h. The reaction mixture was cooled to rt and diethyl ether was added. The suspension was filtered through a pad of silica gel. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (100% hexanes). 2-Bromo-1-methyl-3-(neopentyloxy)benzene was obtained as a colorless oil. The vial was sealed under air atmosphere The reaction mixture was cooled to rt The suspension was filtered through a pad of silica gel The solvent was removed under reduced pressure the remaining residue was purified by flash chromatography (100% hexanes)

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A vial was charged with 2-bromo-1-iodo-3-methylbenzene (677 mg, 2.28 mmol), neopentyl alcohol (2.21 g, 25.08 mmol), copper(I) iodide (43.4 mg, 0.228 mmol), 1,10-phenanthroline (82 mg, 0.456 mmol) and cesium carbonate (1.04 mg, 3.19 mmol). The vial was sealed under air atmosphere and heated to 110° C. for 24 h. The reaction mixture was cooled to rt and diethyl ether was added. The suspension was filtered through a pad of silica gel. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (100% hexanes). 2-Bromo-1-methyl-3-(neopentyloxy)benzene was obtained as a colorless oil. The vial was sealed under air atmosphere The reaction mixture was cooled to rt The suspension was filtered through a pad of silica gel The solvent was removed under reduced pressure the remaining residue was purified by flash chromatography (100% hexanes)