Phenol → 2-Bromoimidazo[5,1-b]thiazole

Temperature

180 °C

A solution of 2-bromoimidazo[5,1-b]thiazole-7-carboxylic acid (31 mg, 0.12 mmol) and phenol (12 mg, 0.12 mmol) dissolved in 1,2,4-trichlorobenzene (1 ml) was stirred at 180° C. for 24 hr. The reaction solution was allowed to cool to room temperature, was diluted with hexane, and was extracted with 1 M hydrochloric acid (3 ml×3). The aqueous layer was neutralized with a 2 M aqueous solution of sodium hydroxide and was extracted with ethyl acetate (5 ml×3). The organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to give 2-bromoimidazo[5,1-b]thiazole (13 mg, 50%) as a white solid.

1. temperatureto cool to room temperature
2. extractionwas extracted with 1 M hydrochloric acid (3 ml×3)
3. extractionwas extracted with ethyl acetate (5 ml×3)
4. washThe organic layer was washed with saturated brine
5. dry with materialwas dried over anhydrous sodium sulfate
6. customThe solvent was removed by distillation under the reduced pressure
7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

ORD record

ord-d5b96680bd9b4229956cf053eaad78d1

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07662841B2