1-iodo-2-(2-methoxyethoxy)benzene

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of commercially available 2-iodo phenol (1 eq.) and 2-bromoethyl methyl ether (1.1 eq) in DMF (0.21M) at 0° C. was added Cs2CO3 (1.5 eq). The mixture was stirred at 50° C. for 6 h, cooled to room temperature, poured in water and extracted with Et2O. The organic extract was washed with water, brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel, eluting with Hex/EtOAc 10%, afforded the desired compound as a colorless oil. cooled to room temperature extracted with Et2O The organic extract was washed with water, brine dried over MgSO4 filtered concentrated Purification by column chromatography on silica gel eluting with Hex/EtOAc 10%

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

Procedure: To a solution of the compound of step 1 (2.20 g, 7.91 mmol) in toluene (20 ml) and THF (4 ml) was added triisopropyl borate (2.19 ml, 9.49 mmol), and the mixture was cooled to −78° C. n-Butyllithium (3.79 ml, 9.49 mmol, 2.5 M in hexane) was added dropwise and the reaction mixture was stirred at −78° C. for 1.5 h. The cooling bath was removed and the reaction mixture was allowed to warm to −20° C. Then 2 N hydrochloric acid (7 ml) was added. When the mixture had reached room temperature, water and EA were added. The organic layer was separated, dried over sodium sulfate, filtered and evaporated in vacuo. The residue was purified by silica gel chromatography (EA/HEP 1:4). 766 mg of the title compound were obtained. was added dropwise The cooling bath was removed to warm to −20° C Then 2 N hydrochloric acid (7 ml) was added had reached room temperature water and EA were added The organic layer was separated dried over sodium sulfate filtered evaporated in vacuo The residue was purified by silica gel chromatography (EA/HEP 1:4)

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

Procedure: To a mixture of 2-iodophenol (5.00 g, 22.7 mmol) and potassium carbonate (4.71 g, 34.1 mmol) in ACN (7 ml) was added 2-bromoethyl methyl ether (3.79 g, 27.3 mmol).