1-bromo-3-chloro-2-methylbenzene

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

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

Procedure: To a solution of 10.0 g (48.7 mmol) 2-bromo-6-chlorotoluene and 11.3 ml (48.7 mmol) triisopropyl borate in 90 ml dry THF were added dropwise 30 ml (49 mmol) of a 1.6 M solution on n-butyllithium in hexanes at −78° C. under argon. After 45 min the reaction mixture was allowed to warm to room temperature. The reaction was quenched by addition of 5 ml water and the solvent was evaporated in vacuo. Addition of 1 M aqueous hydrochloric acid solution was followed by extraction with four portions of dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Crystallisation from heptane gave 5.08 g (61%) of the title compound as a white solid. The reaction was quenched by addition of 5 ml water the solvent was evaporated in vacuo Addition of 1 M aqueous hydrochloric acid solution was followed by extraction with four portions of dichloromethane The combined organic extracts were dried over sodium sulfate concentrated in vacuo Crystallisation from heptane

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

Procedure: 2-bromo-6-chlorotoluene (20.55 g) and N-bromosuccinimide (19.6 g) were stirred together in carbon tetrachloride (100 ml) under reflux for 22 hours exposure to radiation from an infrared lamp. The resulting solution was cooled in ice, filtered and evaporated to yield the title product which was dissolved in petroleum ether (60-80). Part was recrystallised therefrom as pink needles (8.5 g) and part was recovered by evaporation as a dark orange solid (17.7 g) (total yield 26.2 g. 92%). under reflux for 22 hours exposure to radiation from an infrared lamp The resulting solution was cooled in ice filtered evaporated

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

Procedure: 2-bromo-6-chlorotoluene (20.55 g) and N-bromosuccinimide (19.6 g) were stirred together in carbon tetrachloride (100 ml) under reflux for 22 hours exposure to radiation from an infrared lamp. The resulting solution was cooled in ice, filtered and evaporated to yield the title product which was dissolved in petroleum ether (60-80). Part was recrystallised therefrom as pink needles (8.5 g) and part was recovered by evaporation as a dark orange solid (17.7 g) (total yield 26.2 g. 92%). under reflux for 22 hours exposure to radiation from an infrared lamp The resulting solution was cooled in ice filtered evaporated

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

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

Procedure: To a solution of 10.0 g (48.7 mmol) 2-bromo-6-chlorotoluene and 11.3 ml (48.7 mmol) triisopropyl borate in 90 ml dry THF were added dropwise 30 ml (49 mmol) of a 1.6 M solution on n-butyllithium in hexanes at −78° C. under argon. After 45 min the reaction mixture was allowed to warm to room temperature. The reaction was quenched by addition of 5 ml water and the solvent was evaporated in vacuo. Addition of 1 M aqueous hydrochloric acid solution was followed by extraction with four portions of dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Crystallisation from heptane gave 5.08 g (61%) of the title compound as a white solid. The reaction was quenched by addition of 5 ml water the solvent was evaporated in vacuo Addition of 1 M aqueous hydrochloric acid solution was followed by extraction with four portions of dichloromethane The combined organic extracts were dried over sodium sulfate concentrated in vacuo Crystallisation from heptane

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

Procedure: To a solution of 10.0 g (48.7 mmol) 2-bromo-6-chlorotoluene and 11.3 ml (48.7 mmol) triisopropyl borate in 90 ml dry THF were added dropwise 30 ml (49 mmol) of a 1.6 M solution on n-butyllithium in hexanes at −78° C. under argon. After 45 min the reaction mixture was allowed to warm to room temperature. The reaction was quenched by addition of 5 ml water and the solvent was evaporated in vacuo. Addition of 1 M aqueous hydrochloric acid solution was followed by extraction with four portions of dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Crystallisation from heptane gave 5.08 g (61%) of the title compound as a white solid. The reaction was quenched by addition of 5 ml water the solvent was evaporated in vacuo Addition of 1 M aqueous hydrochloric acid solution was followed by extraction with four portions of dichloromethane The combined organic extracts were dried over sodium sulfate concentrated in vacuo Crystallisation from heptane

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

Procedure: 2-bromo-6-chlorotoluene (20.55 g) and N-bromosuccinimide (19.6 g) were stirred together in carbon tetrachloride (100 ml) under reflux for 22 hours exposure to radiation from an infrared lamp. The resulting solution was cooled in ice, filtered and evaporated to yield the title product which was dissolved in petroleum ether (60-80). Part was recrystallised therefrom as pink needles (8.5 g) and part was recovered by evaporation as a dark orange solid (17.7 g) (total yield 26.2 g. 92%). under reflux for 22 hours exposure to radiation from an infrared lamp The resulting solution was cooled in ice filtered evaporated