2,5-Dibromothieno[3,2-b]thiophene

Uses

2,5-Dibromothieno[3,2-b]thiophene is useful in preparation and electronic properties of fused oligothienoacenes.

Synthesis

General procedure for the synthesis of 2,5-dibromothieno[3,2-b]thiophene from thieno[3,2-b]thiophene: Thieno[3,2-b]thiophene (2.01 g, purchased from Tokyo Chemical Industry Co., Ltd.) was added to a reaction vial with 30 mL of N,N-dimethylformamide (DMF). After stirring at room temperature until complete dissolution, N-bromosuccinimide (NBS, 6.10 g, 2.4 eq.) was slowly added. The progress of the reaction was monitored by thin layer chromatography (TLC), and after the complete disappearance of the raw material, hexane and deionized water were added to the reaction mixture for extraction. The organic phase was separated and washed sequentially with deionized water and saturated saline. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure to give 4.21 g of 2,5-dibromothieno[3,2-b]thiophene as a white solid in 99% yield.

References

[1] Patent: TWI630193, 2018, B. Location in patent: Paragraph 0104; 0105
[2] Chemistry - A European Journal, 2011, vol. 17, # 3, p. 866 - 872
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 10, p. 2920 - 2924
[4] Angew. Chem., 2013, vol. 125, # 10, p. 2992 - 2996,5
[5] Tetrahedron Letters, 2009, vol. 50, # 51, p. 7148 - 7151