Carbazole → 3-Bromocarbazole

Participants

Reaction Steps

A preferred example is the use of 3-(2-propenyl)-N-trimethylsilylmethylcarbazole as the polymerizable monomer in a photoresist. 3-Bromocarbazole is prepared by treating carbazole in pyridine with a solution of bromine in pyridine. The purified product is converted to the N-trimethylsilylmethyl derivative by sequential treatment in tetrahydrofuran with sodium hydride and chloromethyltrimethylsilane, followed by refluxing. The purified product is treated with n-butyllithium, acetone, and worked up to give an intermediate alcohol, which is converted to 3(2-propenyl)-N-trimethylsilylmethylcarbazole by treatment with thionyl chloride in pyridine at 50° C. The product is purified by column chromatography to give a very viscous liquid.

Provenance & Evidence