Iodine → 5-(Dimethylamino)-2-iodophenol

HRID 1582477

Reaction equation

HRID 1582477 reaction equation
[I:1]I.C([O-])(=O)C.[Tl+].[CH3:8][N:9]([CH3:17])[C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1>C(Cl)Cl>[CH3:8][N:9]([CH3:17])[C:10]1[CH:15]=[CH:14][C:13]([I:1])=[C:12]([OH:16])[CH:11]=1

Participants

5

Reactant 3

HCID 807IodineHCID 74213-(Dimethylamino)phenolHCID 11247thallium(I) acetate

Product 1

HCID 227211275-(Dimethylamino)-2-iodophenolYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Iodine (6.35 g, 25 mmol) in methylene chloride (300 mL) was added dropwise over 3 h to a stirred suspension of thallium(I) acetate (7.90 g, 30 mmol) and 3-dimethylaminophenol (3.43 g, 25 mmol) in methylene chloride (300 mL). The resulting mixture was stirred at room temperature for 24 h and filtered. Evaporation of the solvents and chromatography of the residue over silica gel using 0-5% diethyl ether in hexanes gave 5-dimethylamino-2-iodophenol (2.35 g, 36%).

Workup

  1. filtrationfiltered
  2. customEvaporation of the solvents and chromatography of the residue over silica gel using 0-5% diethyl ether in hexanes

Sources & evidence

ORD record
ord-b07c42823ffa4a66b123f229ea6a0719
Source dataset
uspto-grants-2004_05
Patent number
US06734302B2

Linked notes

Loading…