1-Bromo-4-ethylbenzene → (4-Bromo-thiophen-2-yl)-(4-ethyl-phenyl)-methanol

Under a nitrogen stream, to a solution of 4-bromo-2-thiophenecarboxaldehyde (10.0 g, 52.3 mmol) in anhydrous THF (100 ml), a hexane solution of n-butyllithium (1.6 M, 34.35 ml, 55.0 mmol) was added dropwise at −78° C. over 5 minutes. After stirring at the same temperature for 10 minutes, a solution of 1-bromo-4-ethylbenzene (10.2 g, 55.0 mmol) in THF (50 ml) was added dropwise. The reaction mixture was stirred at −78° C. for 2 hours and, after addition of saturated aqueous ammonium chloride, was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then evaporated under reduced pressure to remove the solvent. The resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:10)) to give the titled compound (7.1 g, 45%).

1. stirringThe reaction mixture was stirred at −78° C. for 2 hours
2. extractionwas then extracted with ethyl acetate
3. washThe organic layer was washed with saturated aqueous sodium chloride
4. dry with materialdried over anhydrous magnesium sulfate
5. customevaporated under reduced pressure
6. customto remove the solvent
7. customThe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:10))

ORD record

ord-cecab4e5864f49939752292c48b7e931

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07767651B2