4-bromo-2-methyl-1-phenylmethoxybenzene

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

Procedure: In N,N-dimethylformamide (40 mL) was dissolved 4-bromo-2-methyl-phenol (1.87 g), potassium carbonate (4.15 g) and benzyl bromide (1.3 mL) were added to the solution, and the mixture was stirred at room temperature for 2 hours. To the reaction mixture were added water and ethyl acetate, and the liquids were separated. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=98:2 to 95:5) to obtain 1-benzyloxy-4-bromo-2-methylbenzene (2.73 g). were added to the solution the liquids were separated The organic layer was separated washed with saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=98:2 to 95:5)

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

Procedure: In N,N-dimethylformamide (40 mL) was dissolved 4-bromo-2-methyl-phenol (1.87 g), potassium carbonate (4.15 g) and benzyl bromide (1.3 mL) were added to the solution, and the mixture was stirred at room temperature for 2 hours. To the reaction mixture were added water and ethyl acetate, and the liquids were separated. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=98:2 to 95:5) to obtain 1-benzyloxy-4-bromo-2-methylbenzene (2.73 g). were added to the solution the liquids were separated The organic layer was separated washed with saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=98:2 to 95:5)

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

Procedure: To 4-bromo-2-methylphenol (1.25 g, 6.67 mmol) in 20 ml MeCN were added dry K2CO3 (1.84 g, 13.34 mmol, 2 equiv) and benzylbromide (0.872 ml, 7.34 mmol, 1.1 equiv) and reaction is stirred for 24 h at room temperature. Reaction mixture was filtered through Celite, solution was concentrated and purified by silica gel column chromatography (Hexane to 8% EtOAc/Hexane) to give 1.65 g 17 in 89% yield. Rf=0.90 (20% EtOAc/Hexane); Reaction mixture was filtered through Celite, solution was concentrated purified by silica gel column chromatography (Hexane to 8% EtOAc/Hexane)

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

Procedure: In N,N-dimethylformamide (40 mL) was dissolved 4-bromo-2-methyl-phenol (1.87 g), potassium carbonate (4.15 g) and benzyl bromide (1.3 mL) were added to the solution, and the mixture was stirred at room temperature for 2 hours. To the reaction mixture were added water and ethyl acetate, and the liquids were separated. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=98:2 to 95:5) to obtain 1-benzyloxy-4-bromo-2-methylbenzene (2.73 g). were added to the solution the liquids were separated The organic layer was separated washed with saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=98:2 to 95:5)