676331-70-7

Upstream product

• 79-22-1 methyl chloroformate 
• 676331-69-4 2-iodo-3-acetoxy-4-methoxy-5,6-dimethylaniline 
• 118538-99-1 2-methoxy-3,4-dimethyl-5-nitrophenol 
• 147623-19-6 2-methoxy-3,4-dimethyl-5-nitrophenyl acetate 
• 676331-67-2 2-iodo-6-methoxy-4,5-dimethyl-3-nitrophenol 

Downstream Products

• 676331-71-8 N-methoxycarbonyl-2-(2,5-cyclohexadienyl)-3-acetoxy-4-methoxy-5,6-dimethylaniline 
• 75139-38-7 carbazomycin B 

Relevant academic research and scientific papers

Synthesis of carbazomycin B by radical arylation of benzene

Iodination of 2-methoxy-3,4-dimethyl-5-nitrophenol followed by acetylation yields (6-iodo-2-methoxy-3,4-dimethyl-5-nitrophenyl) acetate. Reduction with iron and acetic acid followed by reaction with methyl chloroformate then provides N-methoxycarbonyl-3-acetoxy-2-iodo-4-methoxy-5,6-dimethylaniline. Treatment of this substance in benzene at reflux with tributyltin hydride and a catalytic quantity of diphenyl diselenide leads to the formation of N-methoxycarbonyl-3-acetoxy-2-(2,5-cyclohexadienyl)-4-methoxy-5, 6-dimethylaniline which on exposure to phenylselenenyl bromide affords a phenylselenenyl tetrahydrocarbazole. Oxidation deselenation and rearomatization are achieved by heating with tert-butylhydroperoxide finally affording carbazomycin B after saponification.