p-Toluenesulfonic acid → 2-Iodo-4-(propan-2-yl)phenol

HRID 589671Notes

Reaction equation

HRID 589671 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[I:11]N1C(=O)CCC1=O.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[I:11][C:6]1[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:9]=[CH:8][C:7]=1[OH:10]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 74654-IsopropylphenolHCID 120273N-Iodosuccinimide

Product 1

HCID 126521002-Iodo-4-(propan-2-yl)phenolYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-isopropylphenol (500 mg, 3.67 mmol), N-iodosuccinimide (838 mg, 3.72 mmol) and p-TsOH (70 mg, 0.37 mmol) in CH2Cl2 (25 mL) was stirred at room temperature overnight. The reaction mixture was diluted with CH2Cl2 and washed with water. The organic phase was dried and evaporated to give 820 mg of 2-iodo-4-isopropylphenol (85%). 1H NMR (400 MHz, CDCl3) δ ppm 1.22 (d, J=7.03 Hz, 6 H) 2.82 (spt, J=6.95, 6.65 Hz, 1 H) 6.92 (d, J=8.53 Hz, 1 H) 7.11 (dd, J=8.28, 2.01 Hz, 1 H) 7.50 (d, J=2.01 Hz, 1 H).

Workup

  1. washwashed with water
  2. customThe organic phase was dried
  3. customevaporated

Sources & evidence

ORD record
ord-462e7a671fd549e4be389cf37cbaaf59
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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