Hexane → 2-bromo-N-(2-methoxy-6-nitrophenyl)acetamide

To a flask was added sodium hydride (60% dispersion in mineral oil, 610 mg, 15 mmol) and hexane (2 mL) at 0° C. The supernatant liquid was decanted and the residue was dried under reduced pressure. To this was added THF (20 mL) and a solution of 2-methoxy-6-nitroaniline (2 g, 12 mmol, Kubo, K. et al. J. Med. Chem. 1993, 36, 1772-1784) in THF (20 mL) at 0° C. and stirred at rt for 2 h. To this mixture was added bromoacetyl bromide (1.2 mL, 14 mmol) at 0° C. and stirred at rt for 3 h. Then the reaction mixture was quenched by addition of water (100 mL) and extracted with ethyl acetate (100 mL×2). The combined organic layers were washed with brine (100 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (2/1-1/1) to afford 2.9 g (85%) of the title compound.

1. customThe supernatant liquid was decanted
2. customthe residue was dried under reduced pressure
3. additionTo this was added THF (20 mL)
4. customThen the reaction mixture was quenched by addition of water (100 mL)
5. extractionextracted with ethyl acetate (100 mL×2)
6. washThe combined organic layers were washed with brine (100 mL)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (2/1-1/1)

ORD-Eintrag

ord-de71103f26084e2d94440d5998e4b4d5

Quelldatensatz

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08138177B2