2,6-Lutidine → (2E)-N-(3-bromophenyl)-3-phenylprop-2-enamide

To a solution of 3-bromoaniline (13.1 mL, 120 mmol) in dichloromethane (100 mL) and 2,6-lutidine (21 mL, 180 mmol) at 0° C. was added a solution of cinnamoylchloride (20 g, 120 mmol) in dichloromethane (50 mL) dropwise. The reaction mixture was allowed to reach room temperature and was stirred for 2 hours. It was quenched with potassium phosphate buffer (100 mL, 1M, pH 7) and stirred for 15 minutes. Dichloromethane was removed under reduced pressure. The residue was extracted with ethyl acetate. The organic phase was washed with phosphate buffer (200 mL), dried over sodium sulfate and concentrated to dryness. The residue was crystallized from toluene/hexanes to give the product as colorless solid (33.4 g, 92%).

1. customto reach room temperature
2. customIt was quenched with potassium phosphate buffer (100 mL, 1M, pH 7)
3. stirringstirred for 15 minutes
4. customDichloromethane was removed under reduced pressure
5. extractionThe residue was extracted with ethyl acetate
6. washThe organic phase was washed with phosphate buffer (200 mL)
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated to dryness
9. customThe residue was crystallized from toluene/hexanes

ORD record

ord-8864094f6ab34c809b49abe85eeecb31

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07875715B2