3-Bromothiophene → 3-Dodecylthiophene

To a freshly prepared dodecylmagnesium bromide (from 45 mmoles of dodecyl bromide and 45 mmoles of magnesium) in anhydrous diethyl ether (100 ml) was added 3-bromothiophene (45 mmoles) in diethyl ether (25 ml) at ambient temperature under argon and then bis-(1,2-diphenylphosphino)ethane nickel (II) chloride (0.25 g) was added. The reaction mixture was stirred overnight at ambient temperature and then hydrolyzed with ice and saturated aqueous ammonium chloride. The aqueous layer was extracted with diethyl ether (3×25 ml) and the organic phases were combined, washed with water (3×25 ml), dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude product was purified by distillation in vacuo and then flash chromatography to afford the desired product.

1. extractionThe aqueous layer was extracted with diethyl ether (3×25 ml)
2. washwashed with water (3×25 ml)
3. dry with materialdried over anhydrous magnesium sulfate
4. concentrationconcentrated in vacuo
5. distillationThe crude product was purified by distillation in vacuo

ORD record

ord-803f7b643dc846a6a0a27e5fcd977139

Source dataset

uspto-grants-1988_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04730005