methyl 4,5-dichloro-2-methoxybenzoate

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of LiAlH4 (2.42 g, 64 mmol) in THF (40 mL) at −40° C. under argon, a solution of methyl 4,5-dichloro-2-methoxybenzoate (6 g, 26 mmol) in THF (50 mL) was added dropwise. The reaction mixture was stirred at −5° C. to 5° C. for 1 h. The mixture was cooled to −20° C. and then water (2 mL) and NaOH (15%) aqueous were added. The resulting mixture was stirred for 15 min. The solid was filtered, and the cake rinsed with ethyl acetate. The combined filtrate was dried over Na2SO4 and concentrated in vacuo to afford the crude product (4.6 g). The resulting mixture was stirred for 15 min The solid was filtered the cake rinsed with ethyl acetate The combined filtrate was dried over Na2SO4 concentrated in vacuo

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

Procedure: A mixture of 4,5-dichloro-2-methoxybenzoic acid (8.2 g, 37 mmol) and K2CO3 (11.8 g, 111 mmol) in DMF (100 mL), CH3I (6.3 g, 44 mmol) was added dropwise and the resulting mixture was stirred at room temperature for 16 h. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=10:1) to afford the desired product. was added dropwise The mixture was partitioned between ethyl acetate and water The organic layer was washed with water and brine dried over Na2SO4 concentrated in vacuo The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=10:1)

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

Procedure: A mixture of 4,5-dichloro-2-methoxybenzoic acid (8.2 g, 37 mmol) and K2CO3 (11.8 g, 111 mmol) in DMF (100 mL), CH3I (6.3 g, 44 mmol) was added dropwise and the resulting mixture was stirred at room temperature for 16 h. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=10:1) to afford the desired product. was added dropwise The mixture was partitioned between ethyl acetate and water The organic layer was washed with water and brine dried over Na2SO4 concentrated in vacuo The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=10:1)

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of LiAlH4 (2.42 g, 64 mmol) in THF (40 mL) at −40° C. under argon, a solution of methyl 4,5-dichloro-2-methoxybenzoate (6 g, 26 mmol) in THF (50 mL) was added dropwise. The reaction mixture was stirred at −5° C. to 5° C. for 1 h. The mixture was cooled to −20° C. and then water (2 mL) and NaOH (15%) aqueous were added. The resulting mixture was stirred for 15 min. The solid was filtered, and the cake rinsed with ethyl acetate. The combined filtrate was dried over Na2SO4 and concentrated in vacuo to afford the crude product (4.6 g). The resulting mixture was stirred for 15 min The solid was filtered the cake rinsed with ethyl acetate The combined filtrate was dried over Na2SO4 concentrated in vacuo

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

Procedure: A mixture of 4,5-dichloro-2-methoxybenzoic acid (8.2 g, 37 mmol) and K2CO3 (11.8 g, 111 mmol) in DMF (100 mL), CH3I (6.3 g, 44 mmol) was added dropwise and the resulting mixture was stirred at room temperature for 16 h. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=10:1) to afford the desired product. was added dropwise The mixture was partitioned between ethyl acetate and water The organic layer was washed with water and brine dried over Na2SO4 concentrated in vacuo The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=10:1)