4-bromo-2-fluoro-1-(methoxymethyl)benzene

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared according to General Method 8. To a suspension of NaH (50-60% mineral oil, 8 g, 0.33 mol) in Dry DMF (200 mL) at 0° C. was added (4-bromo-2-fluorophenyl)methanol (27 g, 0.1317 mol). The reaction mixture was stirred for 15 min at 0° C. and then warmed to and stirred at RT for 30 min. The reaction mixture was again cooled to 0° C. and MeI (15 mL, 0.1975 mol) was added drop wise. After addition was complete, the reaction mixture was warmed to room temperature and stirred for 1 h. Ice-water was added and the product was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate, and concentrated under reduced pressure to obtained 4-bromo-2-fluoro-1-(methoxymethyl)benzene (24 g). The title compound was prepared warmed to and stirred at RT for 30 min The reaction mixture was again cooled to 0° C. After addition the reaction mixture was warmed to room temperature stirred for 1 h the product was extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulphate concentrated under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared according to General Method 8. To a suspension of NaH (50-60% mineral oil, 8 g, 0.33 mol) in Dry DMF (200 mL) at 0° C. was added (4-bromo-2-fluorophenyl)methanol (27 g, 0.1317 mol). The reaction mixture was stirred for 15 min at 0° C. and then warmed to and stirred at RT for 30 min. The reaction mixture was again cooled to 0° C. and MeI (15 mL, 0.1975 mol) was added drop wise. After addition was complete, the reaction mixture was warmed to room temperature and stirred for 1 h. Ice-water was added and the product was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate, and concentrated under reduced pressure to obtained 4-bromo-2-fluoro-1-(methoxymethyl)benzene (24 g). The title compound was prepared warmed to and stirred at RT for 30 min The reaction mixture was again cooled to 0° C. After addition the reaction mixture was warmed to room temperature stirred for 1 h the product was extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulphate concentrated under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared according to General Method 8. To a suspension of NaH (50-60% mineral oil, 8 g, 0.33 mol) in Dry DMF (200 mL) at 0° C. was added (4-bromo-2-fluorophenyl)methanol (27 g, 0.1317 mol). The reaction mixture was stirred for 15 min at 0° C. and then warmed to and stirred at RT for 30 min. The reaction mixture was again cooled to 0° C. and MeI (15 mL, 0.1975 mol) was added drop wise. After addition was complete, the reaction mixture was warmed to room temperature and stirred for 1 h. Ice-water was added and the product was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate, and concentrated under reduced pressure to obtained 4-bromo-2-fluoro-1-(methoxymethyl)benzene (24 g). The title compound was prepared warmed to and stirred at RT for 30 min The reaction mixture was again cooled to 0° C. After addition the reaction mixture was warmed to room temperature stirred for 1 h the product was extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulphate concentrated under reduced pressure