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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