Bromine → Andecaliximab

Temperature

55 °C

Bromine (1.55 mL, 30.1 mmol) was added dropwise to a solution of 1-fluoro-3-methoxy-2-nitrobenzene (1.29 g, 7.53 mmol) in acetic acid (15.1 mL). The reaction mixture was warmed to 55° C. and stirred at 55° C. for 17 h, after which time the reaction mixture was concentrated in vacuo to give a crude solid. The crude solid was diluted with saturated sodium bicarbonate solution and extracted with ethyl acetate. Layers were separated and the organic layer was washed with saturated sodium bicarbonate solution, dried with sodium sulfate, filtered, and concentrated in vacuo to give the desired product (1.87 g, 99%) as a yellow solid that was used in further step without purification.

1. concentrationafter which time the reaction mixture was concentrated in vacuo
2. customto give a crude solid
3. extractionextracted with ethyl acetate
4. customLayers were separated
5. washthe organic layer was washed with saturated sodium bicarbonate solution
6. dry with materialdried with sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-4236b756814f442285e1fcaec61f1c8a

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09399640B2