Hydrochloric Acid → 3-Phenylthiophene

Temperature

0 °C

To a mixture of 1.0 mL (10.6 mmol) of 3-bromothiophene, 20 mL of anhydrous ether, 60 mg (0.11 mmol) of 1,3-[Bis(diphenylphosphino)-propane]dichloronickel(II)[NiCl2 (dppp)] under N2 with stirring at 0° C. was slowly added 7.0 mL (14 mmol) of 2.0 M PhMgCl in THF. The reaction was slowly warmed to room temperature. Note that a vigorous exothermic reaction may occur if the Grignard reagent is added too fast or if the reaction is allowed to warm to room temperature to rapidly. After stirring for 3 h, the mixture was warmed to reflux for 2 h, poured into 20 mL of 5% HCl solution, and extracted with 2×20 mL of ether. The combined organic phases were washed with 15 mL of H2O and 15 mL of brine, dried (MgSO4) and concentrated. Crystallization from hexanes provided 0.58 g (34% yield) of 3-phenylthiophene.

1. temperatureThe reaction was slowly warmed to room temperature
2. customNote that a vigorous exothermic reaction
3. additionis added too fast or if the reaction
4. temperatureto warm to room temperature to rapidly
5. stirringAfter stirring for 3 h
6. temperaturethe mixture was warmed
7. temperatureto reflux for 2 h
8. extractionextracted with 2×20 mL of ether
9. washThe combined organic phases were washed with 15 mL of H2O and 15 mL of brine
10. dry with materialdried (MgSO4)
11. concentrationconcentrated
12. customCrystallization from hexanes

ORD record

ord-8e6c673618b8469f976ac0436c3d312d

Source dataset

uspto-grants-2000_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06162824