5-Bromo-3-(trifluoromethyl)-4-isothiazolecarboxylic acid → HCID 90418354, compound

Temperature

0 °C

Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 5-bromo-3-(trifluoromethyl)-1,2-thiazole-4-carboxylic acid (800 mg, 2.90 mmol, 1.00 equiv), tetrahydrofuran (3 mL). This was followed by the addition of BH3 (14.5 mL, 5.00 equiv) dropwise with stirring at 0° C. The resulting solution was stirred overnight at 25° C. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:5). The reaction was then quenched by the addition of 20 mL of methanol. The reaction mixture was heated to reflux for 1 h. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5). This resulted in 200 mg (25%) of [5-bromo-3-(trifluoromethyl)-1,2-thiazol-4-yl]methanol as yellow oil.

1. customInto a 50-mL round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. additionThis was followed by the addition of BH3 (14.5 mL, 5.00 equiv) dropwise
4. stirringThe resulting solution was stirred overnight at 25° C
5. customThe reaction was then quenched by the addition of 20 mL of methanol
6. temperatureThe reaction mixture was heated
7. temperatureto reflux for 1 h
8. customThis resulted in 200 mg (25%) of [5-bromo-3-(trifluoromethyl)-1,2-thiazol-4-yl]methanol as yellow oil

ORD record

ord-5b348f4e9ecb413993fbd88c7cb13113

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1