1-chloro-3-ethoxy-2-fluorobenzene

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

Procedure: 504 g of the compound (b44) was added to a reactor in a nitrogen atmosphere, to which 434 g of bromine was added dropwise over 1 hour in a temperature range of 20 to 40° C., followed by stirring for 30 minutes. The resulting reaction mixture was washed with a saturated sodium thiosulfate aqueous solution, a 10% sodium hydroxide aqueous solution, and water. The residue was subjected to fractional distillation under reduced pressure to obtain 605 g of 1-bromo-2-chloro-4-ethoxy-3-fluorobenzene (C12). The resulting compound (C12) was white solid and had a melting point of 48.0 to 48.5° C. and a boiling point of 88 to 90° C./1 mmHg. was added dropwise over 1 hour in a temperature range of 20 to 40° C. The resulting reaction mixture was washed with a saturated sodium thiosulfate aqueous solution The residue was subjected to fractional distillation under reduced pressure

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

Procedure: The compound (b5) was added dropwise to a reactor having 1,200 g of a 10% sodium hydroxide aqueous solution placed therein over 30 minutes in a temperature range of 20 to 40° C. Thereafter, 462 g of diethyl sulfate was added dropwise thereto over 1 hour in a temperature range of 25 to 35° C., followed by stirring for 5 hours in that temperature range. The resulting organic layer was collected and washed with 200 mL of water in three times, followed by drying, to obtain 505 g of 1-chloro-3-ethoxy-2-fluorobenzene (b44). The resulting liquid was colorless. over 1 hour in a temperature range of 25 to 35° C. The resulting organic layer was collected washed with 200 mL of water in three times by drying

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

Procedure: 504 g of the compound (b44) was added to a reactor in a nitrogen atmosphere, to which 434 g of bromine was added dropwise over 1 hour in a temperature range of 20 to 40° C., followed by stirring for 30 minutes. The resulting reaction mixture was washed with a saturated sodium thiosulfate aqueous solution, a 10% sodium hydroxide aqueous solution, and water. The residue was subjected to fractional distillation under reduced pressure to obtain 605 g of 1-bromo-2-chloro-4-ethoxy-3-fluorobenzene (C12). The resulting compound (C12) was white solid and had a melting point of 48.0 to 48.5° C. and a boiling point of 88 to 90° C./1 mmHg. was added dropwise over 1 hour in a temperature range of 20 to 40° C. The resulting reaction mixture was washed with a saturated sodium thiosulfate aqueous solution The residue was subjected to fractional distillation under reduced pressure

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

Procedure: The compound (b5) was added dropwise to a reactor having 1,200 g of a 10% sodium hydroxide aqueous solution placed therein over 30 minutes in a temperature range of 20 to 40° C. Thereafter, 462 g of diethyl sulfate was added dropwise thereto over 1 hour in a temperature range of 25 to 35° C., followed by stirring for 5 hours in that temperature range. The resulting organic layer was collected and washed with 200 mL of water in three times, followed by drying, to obtain 505 g of 1-chloro-3-ethoxy-2-fluorobenzene (b44). The resulting liquid was colorless. over 1 hour in a temperature range of 25 to 35° C. The resulting organic layer was collected washed with 200 mL of water in three times by drying