Iodine → 2-Iodo-4-methylaniline

HRID 1750822Notes

Reaction equation

HRID 1750822 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[I:14]I.OS([O-])=O.[Na+]>C(Cl)Cl.O>[I:14][C:4]1[CH:3]=[C:2]([CH3:1])[CH:8]=[CH:7][C:5]=1[NH2:6]

Participants

7

Reactant 4

HCID 807IodineHCID 7813p-ToluidineHCID 516892Sodium BicarbonateHCID 23665763Sodium Bisulfite

Product 1

HCID 27640002-Iodo-4-methylanilineYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methylaniline (53.5 g, 500 mmol) in DCM (200 mL) was added a solution of NaHCO3 (50.4 g) in water (500 mL), and then I2(127 g) was added. The mixture was stirred at rt overnight. The mixture was treated with aqueous NaHSO3 and extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, and then concentrated in vacuo to afford the product as brown oil (110 g, yield 95%). 1H NMR (300 MHz, CDCl3): δ 7.48 (dd, J=1.8 & 0.6 Hz, 1H), 6.96 (dd, J=8.1 & 1.8 Hz, 1H), 6.67 (d, J=8.1 Hz, 1H), 3.98 (bs, 2H), 2.22 (s, 3H) ppm.

Workup

  1. extractionextracted with DCM
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04d2e9edc536484bad9324e28c7c02c0
Source dataset
uspto-grants-2015_10
Patent number
US09156860B2

Reaction notes

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