4-Bromoanisole → 3-Bromo-5-(4-methoxyphenyl)-2-methylthiophene

Participants

Reaction Steps

The synthesis starts from commercially available 2-methylthiophene, which is brominated in the 3 and 5 position with bromine. The 3,5-dibromo-2-methylthiophene reacts in a Suzuki coupling with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl) methoxybenzene, made from 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 4-bromoanisole in a grignard reaction to obtain 5-(4′-methoxyphenyl)-3-bromo-2-methylthiophene. This compound is reacts with butyl lithium and octafluorocyclopentene to obtain the reaction product. Another example synthesizes 1,2-bis(2-methyl-5-phenyl-3-thienyl) perfluorocyclopentene, while 1,2-bis(5′-(4″-hydroxyphenyl)-2′-methylthien-3′-yl) perfluorocyclopentene is obtained from 1,2-bis(5′(4″methoxyphenyl)-2′-methylthien-3′-yl) perfluorocyclopentene via reaction with BBr3.

Provenance & Evidence