3-Chloro-4-fluoroaniline → 5-Chloro-4-fluoro-2-iodobenzenamine

HRID 555707Notes

Reaction equation

HRID 555707 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].C1C(=O)N([I:17])C(=O)C1>CC(O)=O>[Cl:1][C:2]1[C:8]([F:9])=[CH:7][C:6]([I:17])=[C:4]([CH:3]=1)[NH2:5]

Participants

4

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 120273N-Iodosuccinimide

Product 1

HCID 247872515-Chloro-4-fluoro-2-iodobenzenamine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-chloro-4-fluoroaniline (12.9 g, 88.9 mmol) and NIS (22.0 g, 97.8 mmol) in AcOH (90 mL) is stirred at RT for 1.5 h. After completion, the reaction mixture is quenched by H2O, DCM is added and the organic layer is washed with brine, dried over MgSO4 and evaporated in vacuo. Silica gel flash chromatography of the residue affords 5-chloro-4-fluoro-2-iodoaniline as a colorless powder; HPLC: AtRet=4.75 min; 1HNMR (CDCl3) 7.40 (d, 1H), 6.75 (d, 1H), 4.00 (bs, 2H).

Workup

  1. customAfter completion, the reaction mixture is quenched by H2O, DCM
  2. additionis added
  3. washthe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-5bc46730a06344e6ad58a1f150ea8a56
Source dataset
uspto-grants-2011_11
Patent number
US08053457B2

Reaction notes

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