Potassium Iodide → 4-ethyl-N-(2-methylpropyl)aniline

Temperature

150 °C

To potassium iodide (5342 mg, 32.2 mmol), [Cp*IrCl2]2 (128 mg, 0.161 mmol) and 4-ethylaniline (2 mL, 16.09 mmol) at room temperature, was added 2-methylpropan-1-ol (5.94 mL, 64.4 mmol), followed by water (10 mL). The reaction vessel was sealed and heated by microwaves (Biotage Initiator) to 150° C. for 90 minutes. After cooling the reaction mixture was diluted with water (10 mL) and dichloromethane (20 mL) then stirred vigorously for 3 minutes. The organic phase was separated by hydrophobic frit. The aqueous phase was diluted with further dichloromethane (10 mL) and again stirred vigorously for 2 minutes, then the organics separated by hydrophobic frit. The combined organic fractions were evaporated in vacuo to give the crude product as a brown oil. The crude was purified by silica (Si) chromatography (0-50% dichloromethane-cyclohexane gradient). The appropriate fractions were combined and evaporated in vacuo to give the required product, 2.612 g, as a pale yellow oil. LCMS [LCMS1] Rt 0.96 min, m/z (ES+) 178 (M+H).

1. customThe reaction vessel was sealed
2. temperatureAfter cooling the reaction mixture
3. customThe organic phase was separated by hydrophobic frit
4. additionThe aqueous phase was diluted with further dichloromethane (10 mL)
5. stirringagain stirred vigorously for 2 minutes
6. customthe organics separated by hydrophobic frit
7. customThe combined organic fractions were evaporated in vacuo
8. customto give the crude product as a brown oil
9. customThe crude was purified by silica (Si) chromatography (0-50% dichloromethane-cyclohexane gradient)
10. customevaporated in vacuo

ORD record

ord-c14daa7dda0946bfbcc74a62eb8bd144

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428452B2