Water → HCID 66937252, compound

Temperature

100 °C

To a solution of phenol (0.500 g, 5.31 mmol) in dry DMF (20 mL) was added solid sodium t-butoxide (0.510 g, 5.31 mmol). The mixture was heated to 100° C. for 60 min, then 4,5-dichloro-2-nitro-phenylamine (1.00 g, 4.83 mmol) was added and the reaction mixture was heated at 100° C. for 19 h. The reaction mixture was allowed to cool to ambient temperature. The reaction mixture was added to water and extracted with EtOAc. The combined organic layers were washed with 1M Na2CO3, dried, filtered, and concentrated under reduced pressure. The residue was purified (FCC) (hexanes:EtOAc, 5% to 30% over 20 minutes) to yield the titled compound as an orange solid (0.821 g, 64%). 1H NMR (400 MHz, CDCl3): 8.27 (s, 1H), 7.50-7.34 (m, 2H), 7.27 (d, J=8.9 Hz, 2H), 7.10 (dd, J=8.6, 1.1 Hz, 2H), 6.02 (s, 3H).

1. temperaturethe reaction mixture was heated at 100° C. for 19 h
2. temperatureto cool to ambient temperature
3. extractionextracted with EtOAc
4. washThe combined organic layers were washed with 1M Na2CO3
5. customdried
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified (FCC) (hexanes:EtOAc, 5% to 30% over 20 minutes)

ORD record

ord-2ee9bf206ca04b949f494819f78a0719

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759345B2