Bromine → 2-Bromo-4-fluoro-6-nitroaniline

HRID 2183911Notes

Reaction equation

HRID 2183911 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[Br:12]Br>O.Br>[Br:12][C:7]1[CH:8]=[C:2]([F:1])[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]=1[NH2:6]

Participants

5

Reactant 2

HCID 24408BromineHCID 677694-Fluoro-2-nitroaniline

Product 1

HCID 2920042-Bromo-4-fluoro-6-nitroanilineYield 94%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

A solution of 4-fluoro-2-nitroaniline (39.03 g, 250 mmol) in water (900 ml) and 48% hydrobromic acid (1500 ml) was treated with bromine (15.26 ml, 46 g, 288 mmol) added dropwise over 20 min. The resulting precipitate was stirred at ambient temperature for a further 45 min then diluted with ice-water (2000 ml). The solid product was collected by filtration, washed with cold water and dried to afford 2-bromo-4-fluoro-6-nitrophenylamine as an orange powder (55 g, 94%): δH (360 MHz, CDCl3) 6.49 (2H, br), 7.56 (1H, dd, J 7 and 3), 7.90 (1H, dd, J 9 and 3).

Workup

  1. additionadded dropwise over 20 min
  2. filtrationThe solid product was collected by filtration
  3. washwashed with cold water
  4. customdried

Sources & evidence

ORD record
ord-2297af95b1ee4565af1ea2f7866c3866
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

Loading…