DOx precursor for Enolate chemistry

[cilliersb]

2,5-Dimethoxy-iodobenzene

Sodium nitrite (6.9 g, 100 mmol, 10 eq) in water (10 ml) was added dropwise to a stirred, ice cooled, solution of 2,5-Dimethoxyaniline (1.83 g, 10 mmol) in water (10 ml) and conc. H2SO4 (1.6 ml, 30 mmol, 3 eq). The reaction was stirred until all starting substituted aniline had disappeared. The yellow solution was then poured into a stirred solution of KI (2.5 g, 15 mmol, 1.5 eq) in water (5 ml). Reaction mixture was extracted with diethyl ether (3x30 ml). The combined organic phases were washed with aqueous Na2SO3 1M (30 ml), water (30 ml), brine (30 ml), dried and evaporated. The obtain solid was recrystallised from ethanol to give 2,5-Dimethoxy-iodobenzene (2.12 g) as colourless plate crystals .

References

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