Hydrazinium, 1,1,1-trimethyl-, iodide (1:1) → 3-(3-Bromo-5-chlorophenoxy)-4-chloro-2-nitroaniline

Temperatur

-40 °C

To copper (I) chloride (5.45 mg, 0.055 mmol) and potassium tert-butoxide (247 mg, 2.204 mmol) suspended in DMF (3 mL) at 0° C. was added 1,1,1-trimethylhydrazinium iodide (139 mg, 0.689 mmol). This mixture was allowed to stir for several minutes at which point the mixture was cooled to −40° C. and 2-(3-bromo-5-chlorophenoxy)-1-chloro-3-nitrobenzene (200 mg, 0.551 mmol) as a solution in DMF (1 mL) was added dropwise. The reaction was maintained at −40° C. for 15 minutes and was then quenched at −40° C. with saturated aqueous ammonium chloride (10 mL). Water (10 mL) was added and the mixture was allowed to warm to room temperature. The mixture was extracted with ethyl acetate (2×50 mL). The combined organic fractions were washed with water (3×50 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by automated column chromatography on silica gel (40 g) eluting with 0-25% EtOAc/hexanes to give the title product. LRMS (M+1)=378.7.

1. temperatureThe reaction was maintained at −40° C. for 15 minutes
2. customwas then quenched at −40° C. with saturated aqueous ammonium chloride (10 mL)
3. additionWater (10 mL) was added
4. temperatureto warm to room temperature
5. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
6. washThe combined organic fractions were washed with water (3×50 mL)
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. customthe solvent was evaporated under reduced pressure
10. customThe resulting residue was purified by automated column chromatography on silica gel (40 g)
11. washeluting with 0-25% EtOAc/hexanes

ORD-Eintrag

ord-ccf239251028453396b0c06c02f3fadb

Quelldatensatz

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07781454B2