Hydrochloric Acid → 2-Phenylthiophene

Temperature

0 °C

Under a nitrogen atmosphere, a mixture of 0.7 gram (catalyst) of bis(1,3-diphenylphosphino)propanenickel (II) chloride in 200 mL of dry diethyl ether was stirred, and 40 grams (0.245 mole) of 2-bromothiophene was added. The mixture was cooled to 0° C., and 113 mL (0.328 mole) of phenylmagnesium bromide (3M in diethyl ether) was added during a 20 minute period. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature and then was heated under reflux for 16 hours. The reaction mixture was poured with shaking into 500 mL of an aqueous 10% hydrochloric acid solution. The organic layer was separated and washed with distilled water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was distilled under vacuum to yield 36 grams of 2-phenylthiophene; b.p. 140° C./3 mm, as a low melting solid.

1. additionUpon completion of addition
2. temperatureto warm to ambient temperature
3. temperaturewas heated
4. temperatureunder reflux for 16 hours
5. additionThe reaction mixture was poured
6. customThe organic layer was separated
7. washwashed with distilled water
8. dry with materialThe organic layer was dried with magnesium sulfate
9. filtrationfiltered
10. concentrationThe filtrate was concentrated under reduced pressure to a residue
11. distillationThe residue was distilled under vacuum

ORD record

ord-2994a0ed8c224337a0f1dc8f3eb2d70f

Source dataset

uspto-grants-1989_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04826829