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

Temperatur

-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-Eintrag

ord-d3c08cba17f84c658fd3e8c877fa8c03

Quelldatensatz

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08153662B2