2-BroMo-4-chloro-6-fluorobenzaldehyde

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

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

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

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-bromo-4-chloro-6-fluoro-benzaldehyde (15 g, 63.16 mmol) in 2-propanol (130 ml) was added hydroxylamine (50% solution in water, 4.55 g, 68.90 mmol) at 25° C. and the mixture was warmed to 40° C. for 2 h. Water (55 ml) was then added slowly to this mixture and the slurry was aged for 1 h at 20° C. The reaction mixture was filtered and the remaining solid was washed with a mixture of 2-propanol and water (1.5:1) and dried under vacuum to yield the title compound (12.5 g, 77%) as white solid. The reaction mixture was filtered the remaining solid was washed with a mixture of 2-propanol and water (1.5:1) dried under vacuum

Conditions: temp:-45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1,2-dibromo-5-chloro-3-fluoro-benzene (10 g, 34.68 mmol) in heptane (27 ml) was added THF (44 ml) and the mixture was cooled to −45° C. Then, iPrMgCl (38.14 ml, 38.14 mmol, 1M solution in THF) was added dropwise to the reaction mixture maintaining the temperature between −40° C. to −45° C. The mixture was stirred for 30 minutes at −40° C. before DMF (13.4 ml, 173.4 mmol) was added dropwise to the reaction mixture maintaining the temperature between −45° C. to −20° C. After stirring for another 15 minutes at −20° C., it was poured into a mixture of 2N HCl (20 ml) and ether (50 ml) at 0° C. The organic layer was separated and the aqueous layer was extracted two times with ether. The combined organic layers were dried with Na2SO4 and evaporated in vacuo to obtain the title compound (7.8 g, 95%) as yellow solid. maintaining the temperature between −40° C. to −45° C was added dropwise to the reaction mixture maintaining the temperature between −45° C. to −20° C The organic layer was separated the aqueous layer was extracted two times with ether The combined organic layers were dried with Na2SO4 evaporated in vacuo

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-bromo-4-chloro-6-fluoro-benzaldehyde (15 g, 63.16 mmol) in 2-propanol (130 ml) was added hydroxyl amine hydrate (50% solution in water, 4.55 g, 68.90 mmol) at 25° C. and the mixture was warmed to 40° C. for 2 h. Water (55 ml) was then added slowly to this mixture and the slurry was aged for 1 h at 20° C. The reaction mixture was filtered and the remaining solid was washed with a mixture of 2-propanol and water (1.5:1) and dried under vacuum to yield the title compound as white solid (12.5 g, 77%). The reaction mixture was filtered the remaining solid was washed with a mixture of 2-propanol and water (1.5:1) dried under vacuum

Conditions: temp:-45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1,2-dibromo-5-chloro-3-fluoro-benzene (10 g, 34.68 mmol) in heptane (27 ml) was added THF (44 ml) and the mixture was cooled to −45° C. Then iPrMgCl (38.14 ml, 38.14 mmol, 1M solution in THF) was added dropwise to the reaction mixture maintaining the temperature between −40° C. to −45° C. The mixture was stirred for 30 minutes at −40° C. before DMF (13.4 ml, 173.4 mmol) was added dropwise to the reaction mixture maintaining the temperature between −45° C. to −20° C. After stirring for another 15 minutes at −20° C., the reaction mixture was poured into a mixture of 2N HCl (20 ml) and ether (50 ml) at 0° C. The organic layer was separated and the aqueous layer was extracted two times with ether. The combined organic layers were dried with Na2SO4 and evaporated in vacuo to obtain the title compound as yellow solid (7.8 g, 95%). maintaining the temperature between −40° C. to −45° C was added dropwise to the reaction mixture maintaining the temperature between −45° C. to −20° C The organic layer was separated the aqueous layer was extracted two times with ether The combined organic layers were dried with Na2SO4 evaporated in vacuo