1,3-Dibromo-2-fluoro-5-nitrobenzene → 3,5-Dibromo-4-fluoroaniline

A 250 ml round bottom flask was charged with iron powder (325 mesh) (2.6 g, 46.6 mmol), 1,3-dibromo-2-fluoro-5-nitrobenzene (2.0 g, 4.01 mmol) and acetic acid (50 ml). The flask was evacuated and back-filled with nitrogen twice, and then stirred at room temperature for 1 hour. The reaction mixture turned into very thick slurry. Acetic acid (50 ml) was added and the mixture stirred for an additional hour. The reaction mixture was poured into EtOAc. The EtOAc solution was washed with water (2×), NaHCO3+Na2CO3 solution until CO2 evolution stopped, then once with brine, then dried over MgSO4, filtered and evaporated to dryness to give 1.6 g crude 3,5-dibromo-4-fluoroaniline (1.6 g). The product was used without further purification in the next experiment.

1. customThe flask was evacuated
2. additionback-filled with nitrogen twice
3. additionAcetic acid (50 ml) was added
4. stirringthe mixture stirred for an additional hour
5. additionThe reaction mixture was poured into EtOAc
6. washThe EtOAc solution was washed with water (2×), NaHCO3+Na2CO3 solution until CO2 evolution
7. dry with materialonce with brine, then dried over MgSO4
8. filtrationfiltered
9. customevaporated to dryness

ORD record

ord-9d3f86c865144975a7c346295739cb97

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273057B2