Sodium Hydroxide → 2-Bromo-5-fluoro-4-nitroaniline

HRID 503307

Reaction equation

HRID 503307 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])[NH2:5].[Br:12]Br.[OH-].[Na+]>CC(O)=O.C(Cl)(Cl)Cl>[Br:12][C:6]1[CH:7]=[C:8]([N+:9]([O-:11])=[O:10])[C:2]([F:1])=[CH:3][C:4]=1[NH2:5]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 754013-Fluoro-4-nitroaniline

Product 1

HCID 574885132-Bromo-5-fluoro-4-nitroanilineYield 90.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

To a mixture of 3-fluoro-4-nitroaniline (6.5 g, 42.2 mmol) in AcOH (80 mL) and chloroform (25 mL) was added dropwise Br2 (2.15 mL, 42.2 mmol) at 0° C. After addition, the resulting mixture was stirred at room temperature for 2 h and then poured into ice water. The mixture was basified with aqueous NaOH (10%) to pH ˜8.0-9.0 under cooling and then extracted with EtOAc (50 mL×3). The combined organic layers were washed with water (80 mL×2) and brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure to give 2-bromo-5-fluoro-4-nitroaniline (9 g, 90%). 1H-NMR (400 MHz, DMSO-d6) δ 8.26 (d, J=8.0, Hz, 1H), 7.07 (brs, 2H), 6.62 (d, J=9.6 Hz, 1H).

Workup

  1. additionAfter addition
  2. temperatureunder cooling
  3. extractionextracted with EtOAc (50 mL×3)
  4. washThe combined organic layers were washed with water (80 mL×2) and brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2c57c9bf886848c88f0fb2579d78fcb9
Source dataset
uspto-grants-2010_08
Patent number
US07776905B2

Linked notes

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