Triethylamine → 1-(5-Bromo-2-chlorophenyl)-2-[methoxy(methyl)amino]ethanone

To a solution of N,O-dimethyl hydroxylamine hydrochloride (1.0 g, 10.25 mmol) in dichloromethane (50 mL) was added triethyl amine (3.10 g, 30.75 mmol). The mixture was stirred at room temperature for 10 min followed by adding 5-bromo-2-chloro-benzoic acid 15a (2.41 g, 10.25 mmol, purchased from Beijing yu xiang hui da chemical co., LTD) and bis(2-oxo-3-oxazolidiny)phosphonic chloride (3.13 g, 12.3 mmol) in turn. The resulting mixture was further stirred for 23 hours. The reaction mixture was quenched with 40 mL of water and extracted with ethyl acetate (40 mL×3). The combined organic layers were washed with saturated brine (50 mL×3), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 15b as a white solid (2.90 g, 100%). The crude product was used in next step without further purification.

1. stirringThe resulting mixture was further stirred for 23 hours
2. customThe reaction mixture was quenched with 40 mL of water
3. extractionextracted with ethyl acetate (40 mL×3)
4. washThe combined organic layers were washed with saturated brine (50 mL×3)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-a3b12eafba6948ee80da2ad1ce292c45

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394329B2