N-Iodosuccinimide → 4-Bromo-5-fluoro-2-iodoaniline

HRID 1504489Notes

Reaction equation

HRID 1504489 reaction equation
[I:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][C:11]=1[F:17]>CC(O)=O.C1(C)C=CC=CC=1>[Br:9][C:10]1[C:11]([F:17])=[CH:12][C:13]([NH2:14])=[C:15]([I:1])[CH:16]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 8218484-Bromo-3-fluoroaniline

Product 1

HCID 686594764-Bromo-5-fluoro-2-iodoanilineYield 87%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

N-iodosuccinimide (2.90 ml, 28.9 mmol) was added to a solution of 4-bromo-3-fluoroaniline (5.00 g, 26.3 mmol) in AcOH (52.6 ml). The reaction was maintained at ambient temperature for 1.5 h, then diluted with 20 mL toluene and concentrated. The residue was dissolved in EtOAc and washed with 2 N aqueous NaOH. The organic phase was washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (40-g Ultra SNAP column, 25-g silica gel loading column, 2-10% EtOAc/Heptane) to give 4-bromo-5-fluoro-2-iodoaniline (7.23 g, 22.89 mmol, 87% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.74-7.78 (m, 1H), 6.53-6.57 (m, 1H). m/z (ESI) 315.9 (M+H)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with 2 N aqueous NaOH
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (40-g Ultra SNAP column, 25-g silica gel loading column, 2-10% EtOAc/Heptane)

Sources & evidence

ORD record
ord-bfb13985fb9f4aa3b206201376e6d64b
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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