Iodine → 2-Iodo-4-methylaniline
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
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of p-toluidine (5 g, 46.7 mmol) in methylene chloride (25 mL) was added a solution of sodium bicarbonate (4.7 g, 56 mmol) in water (75 mL). Then was added iodine (11.26 g, 44.33 mmol) in small portions and the mixture was stirred for 16 hours 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 vacuo to give a crude 2-iodo-4-methylaniline.
Workup
- customThe reaction was quenched with saturated NaHSO3
- extractionthe product was extracted with methylene chloride
- washThe methylene chloride layer was washed with brine
- dry with materialdried over Na2SO4
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-03feabe7ed0f49ca985286056400081a
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06140499
Reaction notes
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