3-Chloro-4-methylaniline → 5-Chloro-2-iodo-4-methylaniline

HRID 272694Notes

Reaction equation

HRID 272694 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[I:10](Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1.C([O-])([O-])=O.[Ca+2]>C(Cl)Cl.CO.CCOCC>[Cl:1][C:2]1[C:8]([CH3:9])=[CH:7][C:6]([I:10])=[C:4]([CH:3]=1)[NH2:5]

Participants

7

Reactant 3

HCID 72553-Chloro-4-methylanilineHCID 10112Calcium CarbonateHCID 56924451Trimethylbenzylammonium Dichloroiodate

Product 1

HCID 584754055-Chloro-2-iodo-4-methylanilineYield 63.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

3-Chloro-4-methylaniline (1.50 g, 10.6 mmol) and benzyltrimethylammonium dichloroiodate (4.60 g, 13.2 mmol) were dissolved in CH2Cl2 (50 mL) and MeOH (20 mL), then CaCO3 (3.10 g, 31.0 mmol) was added and the reaction stirred at room temperature overnight. The reaction was diluted with Et2O (200 mL), filtered through Celite®, and concentrated. The crude material was purified by column chromatography using 97.5/2.5 hexane/EtOAc, giving the product (1.80 g, 63%) as light tan solids. MS (DCI) m/e 268 and 270 (M+H)+; 1H NMR (300 MHz, CDCl3) δ 7.48 (s, 1H), 6.76 (s, 1H), 4.00 (v br s, 2H), 2.22 (s, 3H).

Workup

  1. filtrationfiltered through Celite®
  2. concentrationconcentrated
  3. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-4717a9b5d6464228960f5169b18f2799
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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