1-bromo-2-(2-methoxyethyl)benzene

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

Procedure: To a solution of 2-(2-bromophenyl)ethyl methyl ether (V.2; 1 eq.) in THF (0.16M) at −78° C. was added n-butyllithium (2.5M; 1.1 eq.). The reaction mixture was stirred for 1 h at −78° C. then tri-iso-propylborate (1.2 eq.) was added and the final mixture was allowed to warm slowly to room temperature and stirred for 1 h. The reaction was quenched with the addition of aqueous HCl (1N) and extracted with EtOAc. The organic extract was washed with brine, dried over Na2SO4, filtered and concentrated to afford the desired material as a foam which was used as such. to warm slowly to room temperature stirred for 1 h The reaction was quenched with the addition of aqueous HCl (1N) extracted with EtOAc The organic extract was washed with brine dried over Na2SO4 filtered concentrated

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

Procedure: To a solution of commercially available 2-(2-bromophenyl)ethanol (1 eq.) in THF/DMF (4/1; 0.12M) at 0° C. was added NaH (60% dispersion in oil; 1.5 eq). The mixture was stirred for 30 min then iodomethane (2 eq.) was added. The final mixture was stirred for 12 h at room temperature, poured in saturated aqueous NH4Cl and then extracted with Et2O. The organic extract was washed with water, brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel (Combi Flash from ISCO), eluting with Hex/EtOAc 0 to 50%, afforded the desired compound as a colorless oil. extracted with Et2O The organic extract was washed with water, brine dried over MgSO4 filtered concentrated Purification by column chromatography on silica gel (Combi Flash from ISCO) eluting with Hex/EtOAc 0 to 50%