Boron tribromide → 4-(1,2,3-Thiadiazol-4-Yl)Phenol

Temperature

-78 °C

4-(4-methoxy-phenyl)-[1,2,3]thiadiazole (1.06 g, 5.50 mmol) was dissolved in methylene chloride (20 ml) and the solution was cooled to about −78° C. Boron tribromide (1.0 M in methylene chloride, 12.1 ml) was added dropwise to the solution to afford a brown-colored solution. The reaction mixture was allowed to stir for about fifteen minutes, the cooling bath was removed, and the mixture was allowed to stir at room temperature for about an additional twelve hours. The mixture was poured into water, and the resulting mixture was adjusted to about pH 6. The mixture was extracted with methylene chloride (3×100 ml), and the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to afford 924 mg (94% yield) of the desired title compound as a tan solid. LRMS ([M+H]+)=179.1.

1. customto afford a brown-colored solution
2. customthe cooling bath was removed
3. stirringto stir at room temperature for about an additional twelve hours
4. additionThe mixture was poured into water
5. extractionThe mixture was extracted with methylene chloride (3×100 ml)
6. dry with materialthe combined organic layers were dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-7a97b6e098e742eaa10e136297d75d58

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06566377B2