Greetings. I'm currently trying to do demethylation of aryl compound. Found a method using BBr3 but apparently BBr3 is not allowed in my country. Another method is by using Canonica's approach with addition of iodocyclohexane, unfortunately I don't have enough sample to do according to the method. What is the cheapest and easiest method to do aryl demethylation with limited amount of sample (app. 50mg). Any papers that I can refer to? Thank you.
TMSI prepared in situ with TMSCl and NaI in acetonitrile or HBr are options too.
TMSI is probably the neatest reagent, because all of the by-products are volatile.
The BI3-N(Et)2Ph complex is easily prepared from NaBH4, iodine and diethylaniline, and also cleaves aryl ethers nicely.
Narayana, C.; Padmanabhan, S.; Kabalka, G. W., Tetrahedron Lett., (1990) 31:6977
Kabalka, G. W., Narayana, C., Reddy, N. Synth. Commun. (1992) 22:1793
HBr in AcOH at 80-1200C and NaSMe in DMF also can be tried for O-demethylation.
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