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Reactions of 2‐trimethylsilyl‐3,4‐bis(methoxycarbonyl)furans 1a,b with sulfuryl chloride, bromine, and iodine monochloride in acetonitrile afforded the corresponding 2‐halo‐3,4‐bis(methoxycarbonyl)furans 2a‐f via chloro‐, bromo‐, and iododesilylation in good yields, respectively. However, the reaction of 1a with bromine in carbon tetrachloride mainly gave 2‐bromo‐ 2b and 2‐bromo‐5‐trimethylsilyl‐3,4‐bis(methoxycarbonyl)furan (3) in 37% and 45% yields. Similarly, the reaction of 1a with iodine monochloride afforded 1a, 2‐chloro‐ 2a and 2‐iodo‐3,4‐bis(methoxycarbonyl)furan (2c) in 50%, 27%, and 23% yield.

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Heating the trimethylsilylfurans (I) with dimethyl acetylenedicarboxylate (II) without solvents produces directly the silylfurandicarboxylates (III).