Hydrochloric Acid → 3-(2-Methylphenyl)thiophene

Temperature

-78 °C

To a solution of 2-bromotoluene (11.7 mmol) in tetrahydrofuran (25 mL) at -78° C. under nitrogen was added n-butyllithium in hexane (11.7 mmol) and the resulting yellow suspension stirred for 45 minutes at -78° C. To this suspension at -78° C. was added magnesium bromide etherate (11.5 mmol) and after stirring for 15 minutes at -70° C., the reaction mixture was allowed to warm to ambient temperature over 45 minutes. The resultant solution was added at ambient temperature to a suspension of 3-bromothiophene (11.0 mmol) and bis(1,2-diphenylphosphino)ethane nickel (II) chloride (0.05 mmol) in diethyl ether (25 mL) that has been stirred for 15 minutes. The reaction mixture was heated at reflux for 16 hours and then cooled in an ice bath. To the cooled reaction mixture was added dilute hydrochloric acid (20 mL) and then diethyl ether (50 mL). The organic phase was washed with saturated aqueous sodium bicarbonate, brine and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue fractionated to give Compound 2a as a clear oil (b.p. 110°-114° C./7 mm).

1. stirringafter stirring for 15 minutes at -70° C.
2. temperatureto warm to ambient temperature over 45 minutes
3. stirringhas been stirred for 15 minutes
4. temperatureThe reaction mixture was heated
5. temperatureat reflux for 16 hours
6. temperaturecooled in an ice bath
7. customTo the cooled reaction mixture
8. washThe organic phase was washed with saturated aqueous sodium bicarbonate, brine
9. dry with materialdried over anhydrous sodium sulfate
10. customThe solvent was removed in vacuo

ORD record

ord-b5be5c94b55d421b84705794540957f0

Source dataset

uspto-grants-1986_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04599341