Iodine chloride → Methyl 5-iodo-2-methoxy-4-methylbenzoate

HRID 1877673Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[I:14]Cl>CO>[I:14][C:10]1[C:11]([CH3:13])=[CH:12][C:3]([O:2][CH3:1])=[C:4]([CH:9]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl 2-methoxy-4-methylbenzoate (1.5 g, 8.32 mmol, 1 eq) was dissolved in methanol. To this solution was added dropwise iodine monochloride (6.75 g, 41.6 mmol, 5 eq) in methanol at room temperature. The reaction mixture was heated at 50° C. for 15 h. Finally, methanol was concentrated, diluted with water and extracted with ethyl acetate. The organic layer was washed with 0.1 N HCl (50 ml), water (100 ml) and brine solution (100 ml). The product was purified by column chromatography using 60-120 silica gel and using 5% ethyl acetate/hexane as eluent. Yield: 1.7 g (80%). 1HNMR (400 MHz, CDCl3): δ 2.44 (s, 3H), 3.86 (s, 3H), 3.88 (s, 3H), 6.86 (s, 1H), 8.20 (s, 1H). LCMS: (ES+) m/z=307.0 (M+H).

Workup

concentrationFinally, methanol was concentrated
additiondiluted with water
extractionextracted with ethyl acetate
washThe organic layer was washed with 0.1 N HCl (50 ml), water (100 ml) and brine solution (100 ml)
customThe product was purified by column chromatography

Sources & evidence

ORD record: ord-7a1771dcfc6a4b178460c830a5eb2bed
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309558B2

Reaction notes

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