Toluene → 2-Cyclopropyl 5-nitrobenzenamine

In a 250 mL round bottom flask to a solution of 2-bromo 5-nitroaniline (2.30 g, 10.60 mmol) in toluene (90 mL) tricyclohexylphosphine (0.89 g, 3.18 mmol), Cs2CO3 (17.22 g, 52.99 mmol), cyclopropylboronic acid MIDA ester (2.92 g, 14.84 mmol) and 10 ml de-ionized water were added and the solution was degassed with nitrogen for 30 minutes. To the above solution Pd(OAc)2 (0.36 g, 1.59 mmol) was added under nitrogen and the reaction mixture was refluxed for 12 hours. LC MS analysis of the crude reaction indicated the completion of the reaction. The crude reaction mixture was filtered on Celite pad and the volatiles were removed under reduced pressure. The dark brown oil was worked-up with 2×100 mL ethyl acetate and water (100 mL), dried on MgSO4 and ethyl acetate was evaporated under reduced pressure. The crude reaction mixture was separated by column chromatography to give 2-cyclopropyl-5-nitrobenzeneamine in 70% yield.

1. customthe solution was degassed with nitrogen for 30 minutes
2. temperaturethe reaction mixture was refluxed for 12 hours
3. customLC MS analysis of the crude reaction
4. customthe completion of the reaction
5. customThe crude reaction mixture
6. filtrationwas filtered on Celite pad
7. customthe volatiles were removed under reduced pressure
8. dry with materialdried on MgSO4 and ethyl acetate
9. customwas evaporated under reduced pressure
10. customThe crude reaction mixture
11. customwas separated by column chromatography

ORD record

ord-32711bfdb24d457ea9bcd8fb8af08a8f

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181222B2