Hydrochloric Acid → 2-Isobutylthiophene

Temperature

-78 °C

To a solution of thiophene (1.12 mL, 14.26 mmol) in 35 mL of 9:1 tetrahydrofuran/hexamethylphosphoramide under argon at −78° C. was added n-butyllithium (6.28 mL, 2.5 M in hexanes) and the resulting solution stirred at −78° C. for 20 minutes. Isobutylbromide (1.63 mL, 15.00 mmol) was added dropwise and the resulting solution stirred while warming to room temperature over 2 h before being poured into 100 mL 1 N hydrochloric acid. Organics were extracted with hexanes (3×100 mL), washed with 0.1 N hydrochloric acid (3×50 mL), water and brine (50 mL each), dried with magnesium sulfate, filtered and concentrated to give crude 2-isobutylthiophene. Used without further purification or characterization.

1. stirringthe resulting solution stirred
2. temperaturewhile warming to room temperature over 2 h
3. extractionOrganics were extracted with hexanes (3×100 mL)
4. washwashed with 0.1 N hydrochloric acid (3×50 mL), water and brine (50 mL each)
5. dry with materialdried with magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-37c3d6086fcf42b58a6050ea78a07af4

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315495B2