Maleimide → HCID 67508406, compound

To a solution of 4-bromo-2-fluoroaniline (10.0 g, 52.6 mmol) in aqueous HCl (50 mL) was added aqueous NaNO2 (4.0 g, 57.9 mmol) at 0° C. The reaction mixture was stirred for 30 min. To this was added a solution of maleimide (7.65 g, 78.9 mmol) in acetone (50 mL). The pH was adjusted to 3-3.5 by addition of sodium acetate. To the resultant reaction mixture was added CuCl (1.05 g, 7.9 mmol) and it was stirred at 0° C. for 1 h and at r.t. for 6 h. Finally acetone was evaporated and the reaction mixture was diluted with water (20 mL) and extracted with DCM (2×50 mL). The organic layer was washed with brine (20 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 1:9 EtOAc:Pet. ether) to provide the title compound (2.6 g, 18%) as brown solid.

1. customTo the resultant reaction mixture
2. stirringwas stirred at 0° C. for 1 h and at r.t. for 6 h
3. customFinally acetone was evaporated
4. additionthe reaction mixture was diluted with water (20 mL)
5. extractionextracted with DCM (2×50 mL)
6. washThe organic layer was washed with brine (20 mL)
7. dry with materialdried over anhydrous sodium sulphate
8. concentrationconcentrated in vacuo
9. customThe crude was purified by column chromatography (silica gel, 1:9 EtOAc:Pet. ether)

ORD record

ord-275378196076419d90fe77f2d178ad7b

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906913B2