A simple one-pot synthesis of hydroxylated and carboxylated aryl alkyl sulfides from various bromobenzenes

A simple one-pot synthesis of aryl alkyl sulfides from various bromobenzenes containing a hydroxy, hydroxymethyl, hydroxyethyl, and carboxylic acid group at -o, -m, and -p positions is reported here. The reaction proceeds through, in sequence, in situ protection of the hydroxy or carboxylic acid group by reaction with a Grignard reagent, lithium-halogen exchange, the formation of lithium thiolates, and the nucleophilic attack of lithium thiolates on various electrophiles without isolation of the thiolates, in one vessel. This procedure required a very short reaction time (1-1.5 h) and gave the corresponding sulfides in 75-97% yields. (c) 2006 Elsevier Ltd. All rights reserved.