m-Chloroperbenzoic acid → 1-Iodo-2-(methylsulfinyl)benzene

HRID 735319Notes

Reaction equation

HRID 735319 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=C[CH:11]=1)[C:5]([O:7]O)=[O:6].[I:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19][CH3:20].[OH-:21].[Ca+2].[OH-]>ClCCl>[C:5]([O:7][CH2:13][CH3:14])(=[O:6])[CH3:4].[CH3:11][CH2:2][CH2:3][CH:4]([CH3:9])[CH3:5].[I:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19]([CH3:20])=[O:21]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 28014161-Iodo-2-methylsulfanylbenzeneHCID 6093208Calcium Hydroxide

Product 2

HCID 21882781Isohexane ethyl acetateYield 40%HCID 532566751-Iodo-2-(methylsulfinyl)benzeneYield 175.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperoxybenzoic acid (77%, 2.7 g, 11.99 mmol) was added to a solution of 2-iodothioanisole (3 g, 11.99 mmol) in dichloromethane (50 mL). The reaction was stirred for 1 hour. Calcium hydroxide (1.33 g, 18 mmol) was added and the mixture stirred for 15 minutes. The solid was removed by filtration through Hyflo®, washing well with dichloromethane. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 20% then 40% ethyl acetate/isohexane, to give 1-iodo-2-(methylsulfinyl)benzene as a colourless oil (2.8 g, 88%). 1H NMR (500 MHz, CDCl3) δ 7.92 (1H, d, J=7.8 Hz), 7.82 (1H, d, J=7.8 Hz), 7.62 (1H, t, J=7.6 Hz), 7.23-7.21 (1H, m), 2.79 (3H, s).

Workup

  1. stirringthe mixture stirred for 15 minutes
  2. customThe solid was removed by filtration through Hyflo®
  3. washwashing well with dichloromethane
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica
  6. washeluting with 20%

Sources & evidence

ORD record
ord-261d9a0375d14a6db6b22934d20fc460
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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