Tetrahydrofuran → (5-Bromo-thiophen-2-yl)-p-tolyl-methanol

Temperature

-78 °C

To an anhydrous tetrahydrofuran (70.0 mL) solution of 2,5-dibromothiophene (5.00 g, 19.6 mmol) was added dropwise n-butyl lithium (2.55 M n-hexane solution, 7.69 mL, 19.6 mmol) on a dry ice-ethanol bath (−78° C.) under nitrogen atmosphere, which was stirred for 20 minutes at −78° C. p-Tolaldehyde (2.35 g, 19.6 mmol) was then added dropwise and stirred for 10 minutes at −78° C. The reaction mixture was allowed to room temperature and water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:5→1:1) to obtain the title compound (4.30 g, 77.5%).

1. additionwas then added dropwise
2. stirringstirred for 10 minutes at −78° C
3. customwas allowed to room temperature
4. extractionfollowed by extraction with ethyl acetate
5. washThe organic layer was washed with saturated aqueous sodium chloride
6. customthe solvent was evaporated under a reduced pressure
7. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:5→1:1)

ORD record

ord-b8f4346876a346f1a158cb653600e3d9

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841327B2