3-Bromothiophene

Uses3-Bromothiophene can be used as a reactant to synthesize:3,3-Bithiophene via borylation followed by Suzuki coupling.3-Alkylthiophenes by NiDPPP++ catalyzed cross-coupling with Grignard reagents.3-Lithiothiophene by treating with n-butyllithium in hexane.Derivatives of thienylenic α, ωdiformylαoligothiophenes.N-(2-(3-bromothiophen-2-yl)phenyl)methanesulfonamides by coupling at the 2-position with N-arylmethanesulfonamides, mediated by iodobenzene diacetate (178721).

Uses3-Bromothiophene is used in the preparation of derivatives such as thienylenic alpha, μ-diformyl-alpha-oligothiophenes and 3-lithiothiophene. It is also used in the synthesis of 3-lithiothiophene by reacting with n-butyllithium.

PreparationPreparation of 3-bromothiophene using 2,5-dibromothiophene2,5-Dibromothiophene (121g, 0.5 moles), tris (3,6-dioxaheptyl) amine (1.0g, 0.003 mole), thiophene (500 cm3) and sodium amide (58.5g, 1.5 mole) were successively charged to a flask which had previously been purged with nitrogen. The reaction mixture was stirred and heated under nitrogen at 50-60°C for 6 hours. The product, after work up as described in Example 3, was found to contain 138.5g 3-bromothiophene and 2.6g 2-bromothiophene. The yield of 3-bromothiophene was 85% and the monobromothiophenes were in the ratio of 2 parts 2-bromothiophene to 98 parts 3-bromothiophene.