Thiophene → 2-(4-bromobutyl)-thiophene

To a solution of thiophene (50 g, 594 mmol) in anhydrous THF (200 mL) is added slowly a 1.6M solution of n-butyllithium in hexane (408 mL, 653 mmol) under nitrogen atmosphere at −30° C. The reaction mixture is stirred for a further 2 hours, during which period it is allowed to warm to room temperature. The solution is recooled to 0° C. and a solution of 1,4-dibromobutane (141 g, 653 mmol) in anhydrous THF (100 mL) is added. The stirring is continued overnight. The mixture is diluted with ethyl acetate (1000 mL) and shaken with water (800 mL). The organic layer is washed with brine twice and dried over anhydrous Na2SO4. After removal of the solvent, the residue is distilled in vacuo to afford 2-(4-bromobutyl)-thiophene 1 as colorless oil (66 g).

1. customis recooled to 0° C.
2. waitThe stirring is continued overnight
3. washThe organic layer is washed with brine twice
4. dry with materialdried over anhydrous Na2SO4
5. customAfter removal of the solvent
6. distillationthe residue is distilled in vacuo

ORD record

ord-929ec18157dc48a9939cff19de890ba3

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07910753B2