Iodine → 4-Iodo-1-(3-methoxyphenyl)-2-methylbenzene

HRID 1700995Notes

Reaction equation

N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)=[C:4]([CH3:16])[CH:3]=1.[I:17]I.N(OCCC(C)C)=O>C1(C)C=CC=CC=1>[I:17][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)=[C:4]([CH3:16])[CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A stirred solution of 4-amino-1-(3-methoxyphenyl)-2-methylbenzene (5.0 gm 23.4 mmol) and iodine (2.97 gm, 25.8 mmol) in toluene (120 mL) was heated to 50° C. and a solution of iso-amyl nitrite (3.46 mL, 25.8 mmol) in toluene (50 mL) was added. The mixture was heated at 90° C. for 2 h and cooled. The toluene was removed under reduced pressure and the residue was dissolved in dichloromethane and washed with excess 5% aqueous sodium metabisulphite to remove iodine. The organic solution was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by repeated flash chromatography (first column gradient elution with hexane:ethyl acetate starting with neat hexane; second column eluted with hexane) to give 4-iodo-1-(3-methoxyphenyl)-2-methylbenzene as a pale orange oil (5.63 gm, 74%).

Workup

temperaturecooled
customThe toluene was removed under reduced pressure
dissolutionthe residue was dissolved in dichloromethane
washwashed with excess 5% aqueous sodium metabisulphite
customto remove iodine
dry with materialThe organic solution was dried (Na2SO4)
concentrationconcentrated under reduced pressure
customThe residue was purified by repeated flash chromatography (first column gradient elution with hexane:ethyl acetate starting with neat hexane; second column eluted with hexane)

Sources & evidence

ORD record: ord-e838b16678bf48e7a891784cb3c9316b
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350907B1

Reaction notes

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