Nitrogen → 3-(3-Bromo-5-chlorophenoxy)-4-chlorobenzene-1,2-diamine

Participants

Reaction Conditions

Reaction Steps

3-(3-bromo-5-chlorophenoxy)-4-chloro-2-nitroaniline (5.7 g, 15 mmol) and tin(II) chloride dihydrate (17 g, 75 mmol) were suspended in MeOH (100 mL) and heated to 75° C. under a reflux condenser and N2. After 10 hours, the reaction was allowed to cool to room temperature. The reaction was concentrated under reduced pressure, diluted with ethyl acetate (150 mL) and 10% aqueous sodium carbonate (250 mL) was added with vigorous stirring until the pH was 10. The mixture was filtered through celite. The resulting biphasic filtrate was separated and the aqueous extracted again with ethyl acetate (150 mL). The combined organic fractions were dried (MgSO4), filtered and the solvent was evaporated under reduced pressure to yield the title product. LRMS (M+1)=348.7.

Provenance & Evidence