Iodine → 2-Iodo-4-methylaniline

HRID 1750834Notes

Reaction equation

HRID 1750834 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[I:14]I>C(Cl)Cl.O>[I:14][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

6

Reactant 3

HCID 807IodineHCID 7813p-ToluidineHCID 516892Sodium Bicarbonate

Product 1

HCID 27640002-Iodo-4-methylanilineYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of p-toluidine (50 g, 467 mmol) in methylene chloride (250 mL) was added a solution of sodium bicarbonate (47 g, 560 mmol) in water (750 mL). Then it was added iodine (118.6 g, 467 mmol) in small portions and the mixture was stirred for 16 h at room temperature. The reaction was quenched with saturated NaHSO3 and the product was extracted with methylene chloride. The methylene chloride layer was washed with brine, dried over Na2SO4, and evaporated in vacuum to give the crude product (100 g, yield 92%). 1H NMR (300 MHz, CDCl3): δ 7.46 (s, 1H), 7.13-6.95 (d, 1H), 6.68-6.64 (d, 1H), 4.00 (br, 2H), 2.21 (s, 3H). MS: m/z 234 [M+1]+.

Workup

  1. customThe reaction was quenched with saturated NaHSO3
  2. extractionthe product was extracted with methylene chloride
  3. washThe methylene chloride layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuum

Sources & evidence

ORD record
ord-cc5c7307eee54d26bfaf0c87ff00ef18
Source dataset
uspto-grants-2015_10
Patent number
US09156860B2

Reaction notes

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