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

HRID 1847742Notes

Reaction equation

HRID 1847742 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH2:11].[Br:12]Br.C([O-])(O)=O.[Na+]>CC(O)=O>[Br:12][C:4]1[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([F:1])[C:3]=1[NH2:11]

Participants

5

Reactant 3

HCID 24408BromineHCID 1012542-Fluoro-4-nitroanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 143001412-Bromo-6-fluoro-4-nitroanilineYield 99.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2-fluoro-4-nitro-phenylamine (12 g, 77 mmol) in AcOH (50 mL) was added Br2 (3.9 mL, 77 mmol) dropwise at 0° C. The mixture was stirred at 20° C. for 3 h. The reaction mixture was basified with sat. aq. NaHCO3, and extracted with EtOAc (100 mL×3). The combined organics were dried over anhydrous Na2SO4 and evaporated under vacuum to give 2-bromo-6-fluoro-4-nitro-phenylamine (18 g, 97%). 1H NMR (400 MHz, CDCl3) δ 8.22 (m, 1H), 7.90 (dd, J=2.4, 10.8 Hz, 1H), 4.88 (brs, 2H).

Workup

  1. extractionextracted with EtOAc (100 mL×3)
  2. dry with materialThe combined organics were dried over anhydrous Na2SO4
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-4004fbdacc2a4e78bdb8562a501a5023
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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