Methyl Acrylate → HCID 23003313, compound

Temperature

80 °C

To a mixture of 2-bromo-5-fluoroaniline (35.00 g, 184 mmol, Aldrich), palladium (II) acetate (2.06 g, 9.18 mmol, Strem) and tri(o-tolyl)phosphine (5.60 g, 18.40 mmol; Strem) in acetonitrile (350 ml) at RT was added methyl acrylate (33.00 ml, 365 mmol, Aldrich) and triethylamine (64.00 ml, 460 mmol, Aldrich). The reaction was heated at 80° C. for 24 h. The reaction mixture was diluted with EtOAc (500 mL) and the resulting colorless crystalline solid was filtered and washed with EtOAc. The organic solution was concentrated to dryness and the solids were slurried in 10% EtOAc/hexane at 60° C. for 1 h. The slurry was cooled to RT and filtered. The solid was washed with 10% EtOAc/hexane and sucked dry with air to give 18.30 g (51%) of a light-yellow crystalline solid. m/z=195.9 (M+1).

1. filtrationthe resulting colorless crystalline solid was filtered
2. washwashed with EtOAc
3. concentrationThe organic solution was concentrated to dryness
4. temperatureThe slurry was cooled to RT
5. filtrationfiltered
6. washThe solid was washed with 10% EtOAc/hexane
7. customsucked dry with air

ORD record

ord-152ddaa6c7004662b8a3ad4e294546be

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09303028B2