4-Bromothiazole

Description

4-Bromothiazole is a chemical intermediate used in the pharmaceutical and agrochemical industries. It is commonly used as a starting material for the synthesis of various heterocyclic compounds, such as thiazoles, which have diverse applications in medicinal chemistry. This product should be handled with care due to its toxic nature. It should be stored in a cool, dry place away from incompatible materials such as oxidizing agents or strong bases.

Uses

4-Bromothiazole is an important pharmaceutical intermediate widely used in the construction of various thiazole heterocyclic compounds, and is commonly applied in new drug development, fine chemicals and other fields.

Synthesis

a) Synthesis of 4-bromothiazole: 10.0 g (41.2 mmol) of 2,4-dibromothiazole was dissolved in 210 mL of ether, and the solution was cooled to -78 °C. Under stirring, 28.3 mL (45.3 mmol, 15% in hexane) of n-butyllithium solution was slowly added dropwise. After the dropwise addition was completed, the reaction mixture was kept at -78 °C and stirring was continued for 30 minutes. Subsequently, 3.3 mL (82.3 mmol) of methanol was slowly added to the reaction mixture. The reaction system was gradually warmed up to room temperature over 16 hours. Upon completion of the reaction, the mixture was filtered through a silica gel pad and washed with a solvent mixture of hexane/ethyl acetate (2:1, v/v). The filtrate and washings were combined and concentrated under reduced pressure to give 6.7 g (40.9 mmol, 99% yield) of 4-bromothiazole.

References

[1] Patent: US2008/261996, 2008, A1. Location in patent: Page/Page column 44
[2] Journal of Materials Chemistry C, 2017, vol. 5, # 45, p. 11927 - 11936
[3] Journal of Organic Chemistry, 2006, vol. 71, # 10, p. 3754 - 3761
[4] Tetrahedron Letters, 1995, vol. 36, # 51, p. 9293 - 9296
[5] Patent: US4990520, 1991, A