3-bromo-N,N-dimethylbenzamide

Conditions: temp:-80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 38.5 g (0.225 mol) of 4-bromotoluene in 450 mL of THF, 300 mL (0.450 mol) of 1.5 M tBuLi in pentane was added dropwise with vigorous stirring for 2 hr at −80° C. This mixture was slowly warmed to room temperature and additionally stirred at this temperature for 30 min. To this mixture 52.0 g (0.23 mol) of 3-bromo-N,N-dimethylbenzamide was added at 0° C., and then this mixture was stirred for 12 hr at room temperature. Later, 300 mL of water was added, organic solvent was evaporated using a rotary evaporator. The product was extracted with 2×200 mL of dichloromethane. The combined organic extracts were evaporated to dryness, and the residue was dried in vacuum. This procedure gave 51.3 g (83%) of 40 which was further used without additional purification. This mixture was slowly warmed to room temperature additionally stirred at this temperature for 30 min this mixture was stirred for 12 hr at room temperature organic solvent was evaporated a rotary evaporator The product was extracted with 2×200 mL of dichloromethane The combined organic extracts were evaporated to dryness the residue was dried in vacuum

Conditions: temp:-80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 8.25 g (52.5 mmol) of bromobenzene in 100 mL of THF, 70 mL (105 mmol) of 2.5 M tBuLi in pentane was added dropwise with vigorous stirring for 2 h at −80° C. This mixture was slowly warmed to room temperature and then stirred for 30 min at this temperature. 11.4 g (50 mmol) of 3-bromo-N,N-dimethylbenzamide was added at 0° C., and the resulting mixture was stirred for 12 hr at room temperature. 150 mL of water was added, the organic solvent was evaporated using a rotary evaporator, and the product was extracted with 2×100 mL of dichloromethane. The combined extracts were dried over K2CO3 and then evaporated to dryness. This procedure gave 12.2 g (89%) of 16 which was further used without an additional purification. This mixture was slowly warmed to room temperature stirred for 30 min at this temperature the resulting mixture was stirred for 12 hr at room temperature the organic solvent was evaporated a rotary evaporator the product was extracted with 2×100 mL of dichloromethane The combined extracts were dried over K2CO3 evaporated to dryness

Conditions: temp:-80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 38.5 g (0.225 mol) of 4-bromotoluene in 450 mL of THF, 300 mL (0.450 mol) of 1.5 M tBuLi in pentane was added dropwise with vigorous stirring for 2 hr at −80° C. This mixture was slowly warmed to room temperature and additionally stirred at this temperature for 30 min. To this mixture 52.0 g (0.23 mol) of 3-bromo-N,N-dimethylbenzamide was added at 0° C., and then this mixture was stirred for 12 hr at room temperature. Later, 300 mL of water was added, organic solvent was evaporated using a rotary evaporator. The product was extracted with 2×200 mL of dichloromethane. The combined organic extracts were evaporated to dryness, and the residue was dried in vacuum. This procedure gave 51.3 g (83%) of 40 which was further used without additional purification. This mixture was slowly warmed to room temperature additionally stirred at this temperature for 30 min this mixture was stirred for 12 hr at room temperature organic solvent was evaporated a rotary evaporator The product was extracted with 2×200 mL of dichloromethane The combined organic extracts were evaporated to dryness the residue was dried in vacuum

Conditions: temp:-80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 8.25 g (52.5 mmol) of bromobenzene in 100 mL of THF, 70 mL (105 mmol) of 2.5 M tBuLi in pentane was added dropwise with vigorous stirring for 2 h at −80° C. This mixture was slowly warmed to room temperature and then stirred for 30 min at this temperature. 11.4 g (50 mmol) of 3-bromo-N,N-dimethylbenzamide was added at 0° C., and the resulting mixture was stirred for 12 hr at room temperature. 150 mL of water was added, the organic solvent was evaporated using a rotary evaporator, and the product was extracted with 2×100 mL of dichloromethane. The combined extracts were dried over K2CO3 and then evaporated to dryness. This procedure gave 12.2 g (89%) of 16 which was further used without an additional purification. This mixture was slowly warmed to room temperature stirred for 30 min at this temperature the resulting mixture was stirred for 12 hr at room temperature the organic solvent was evaporated a rotary evaporator the product was extracted with 2×100 mL of dichloromethane The combined extracts were dried over K2CO3 evaporated to dryness

Conditions: temp:-80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 38.5 g (0.225 mol) of 4-bromotoluene in 450 mL of THF, 300 mL (0.450 mol) of 1.5 M tBuLi in pentane was added dropwise with vigorous stirring for 2 hr at −80° C. This mixture was slowly warmed to room temperature and additionally stirred at this temperature for 30 min. To this mixture 52.0 g (0.23 mol) of 3-bromo-N,N-dimethylbenzamide was added at 0° C., and then this mixture was stirred for 12 hr at room temperature. Later, 300 mL of water was added, organic solvent was evaporated using a rotary evaporator. The product was extracted with 2×200 mL of dichloromethane. The combined organic extracts were evaporated to dryness, and the residue was dried in vacuum. This procedure gave 51.3 g (83%) of 40 which was further used without additional purification. This mixture was slowly warmed to room temperature additionally stirred at this temperature for 30 min this mixture was stirred for 12 hr at room temperature organic solvent was evaporated a rotary evaporator The product was extracted with 2×200 mL of dichloromethane The combined organic extracts were evaporated to dryness the residue was dried in vacuum

Conditions: temp:-80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 8.25 g (52.5 mmol) of bromobenzene in 100 mL of THF, 70 mL (105 mmol) of 2.5 M tBuLi in pentane was added dropwise with vigorous stirring for 2 h at −80° C. This mixture was slowly warmed to room temperature and then stirred for 30 min at this temperature. 11.4 g (50 mmol) of 3-bromo-N,N-dimethylbenzamide was added at 0° C., and the resulting mixture was stirred for 12 hr at room temperature. 150 mL of water was added, the organic solvent was evaporated using a rotary evaporator, and the product was extracted with 2×100 mL of dichloromethane. The combined extracts were dried over K2CO3 and then evaporated to dryness. This procedure gave 12.2 g (89%) of 16 which was further used without an additional purification. This mixture was slowly warmed to room temperature stirred for 30 min at this temperature the resulting mixture was stirred for 12 hr at room temperature the organic solvent was evaporated a rotary evaporator the product was extracted with 2×100 mL of dichloromethane The combined extracts were dried over K2CO3 evaporated to dryness

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

Procedure: Following the general method as outlined in Intermediate 20, starting from (4-chloro-2-ethynyl-phenoxy)-acetic acid tert-butyl ester (Intermediate 3) and 3-bromo-N,N-dimethylbenzamide (Intermediate 180), the title compound was obtained as a brown sticky solid after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

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

Procedure: Following the general method as outlined in Intermediate 174, starting from 3-bromobenzoyl chloride and dimethylamine, the title compound was obtained as a orange sticky solid in 85% yield.

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

Procedure: Following the general method as outlined in Intermediate 174, starting from 3-bromobenzoyl chloride and dimethylamine, the title compound was obtained as a orange sticky solid in 85% yield.