1-iodo-2-methoxybenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Iodoanisole (1.30 mL, 0.01 mol), 2-hydroxypyridine (0.95 g, 0.01 mol), anhydrous K2CO3 (2.76 g, 0.02 mol) and copper powder (0.0636 g, 0.001 mol) were combined and heated at 200° C. for 2 hr. The reaction mixture was cooled, EtOAc added, and filtered. The filtrate was washed with H2O, aqueous saturated NaHCO3 solution, brine, and dried (Na2SO4). Filtration and concentration gave the title compound after chromatography (silica gel, 2% CH3OH, CH2Cl2). The reaction mixture was cooled filtered The filtrate was washed with H2O, aqueous saturated NaHCO3 solution, brine dried (Na2SO4) Filtration and concentration

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a stirred, cold (-78° C.) solution of 2-iodoanisole (2.85 ml, 5.6 g) in 50 ml of tetrahydrofuran under nitrogen was added 10.0 ml of 2.5M n-butyl lithium in hexane. After 15 min. triisopropyl borate (3.38 ml, 4.7 g) was added and the reaction was allowed to come to and remain at room temperature for 1.5 hr. The mixture was poured into an excess of 2N hydrochloric acid and diethyl ether was added. The resulting mixture was stirred vigorously for 30 min. and the phases were separated. The ether layer was washed with aqueous sodium bisulfite until colorless and then with saturated sodium chloride solution and then dried over magnesium sulfate. Concentration of the ether layer gave the crude boronic acid which crystallized from ether to give the title product. was added the phases were separated The ether layer was washed with aqueous sodium bisulfite until colorless and then with saturated sodium chloride solution dried over magnesium sulfate Concentration of the ether layer gave the crude boronic acid which crystallized from ether