Tetrahydrofuran → (2-Bromo-4-fluorobenzo[d]thiazol-6-yl)methanol

To a solution of methyl 2-bromo-4-fluorobenzo[d]thiazole-6-carboxylate 0.335 g, 1.15 mmol) in toluene (10 mL) and THF (5 mL) was added Dibal-H (4.8 mL, 4.8 mmol) at −78° C. over 10 min. The resulting mixture was allowed to warm to rt and stirred at rt for 3 hr before it was poured into ice cold water (100 mL). The mixture was stirred at rt for 30 min and then filtered through Celite® 545. The organic layer was separated and the aqueous layer was extracted twice with AcOEt. The combined organic phase was dried over anhydrous MgSO4 and concentrated under vacuum. Evaporation of solvent under vacuum gave the title compound (0.269 g, 89% yield) as a white solid.

1. stirringThe mixture was stirred at rt for 30 min
2. filtrationfiltered through Celite® 545
3. customThe organic layer was separated
4. extractionthe aqueous layer was extracted twice with AcOEt
5. dry with materialThe combined organic phase was dried over anhydrous MgSO4
6. concentrationconcentrated under vacuum
7. customEvaporation of solvent under vacuum

ORD record

ord-18e8da69cd2349fd891a492f8811eac3

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07473784B2