Yield:-

Steps:

Multi-step reaction with 7 steps
1.1: sodium hydroxide / ethanol / 10 h / 20 °C
2.1: tetrabutylammomium bromide; palladium diacetate; sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 120 °C / Inert atmosphere
3.1: bromine / chlorobenzene / 1 h / 50 °C
4.1: chlorobenzene; methanol / 1 h / 40 °C
5.1: hydrogenchloride / ethanol; water / 2 h / 60 °C
5.2: 2 h / 60 - 80 °C
6.1: tetrabutyl-ammonium chloride; sodium hydroxide / acetonitrile / 5 h / 20 °C
7.1: acetic acid; sulfuryl dichloride / chlorobenzene / 1 h / 40 °C
7.2: 9 h / 100 °C

References:

NIHON NOHYAKU COMPANY LIMITED;KUBOTA, SHUHEI JP2017/206453, 2017, A

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