Electric Literature of 5876-51-7, A common heterocyclic compound, 5876-51-7, name is 5-Iodobenzo[d][1,3]dioxole, molecular formula is C7H5IO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
[00233] To 24.7 mg PdCl2[(PPh2(CH2)5PPh2] in a reaction tube under nitrogen was added 4 ml dioxane and 0.43 ml (3.0 mmol) of triethylamine. The mixture was heated at 80 C. to give an orange coloured solution which still contained solids, presumably PdCl2[(PPh2(CH2)5PPh2]. To this mixture, at room temperature, were added 0.23 ml (1.5 mmol) pinacolborane (solution became brown but still contained insolubles) and 255 mg (1.03 mmol) 1-iodo-3,4-methylenedioxybenzene. The reaction solution was warmed to 80 C. with stirring in an oil bath. Analysis of the reaction solution by gc, as described above, was carried out at intervals (see Table 20.1). The reaction was complete after 5 h reaction time. The reaction solution was a bright crimson colour at the completion of the reaction and the only solids present on cooling to room temp. appeared to be the triethylamine salt. The amount of pinacol ester of phenylboronic acid formed is low with PdCl2[(PPh2(CH2)5PPh2] as catalyst and forms only later in the reaction. [TABLE-US-00009] TABLE 20.1 Rate of product formation on reaction of 1-iodo-3,4-methylenedioxybenzene with pinacolborane at 80 C. The catalyst PdCl2[(PPh2(CH2)5PPh2] was heated with the base triethylamine (3.0 mmol) prior to reaction. The concentrations are expressed in area % (uncorrected for response factors) determined by gc analysis of aliquots of the reaction solution taken at selected reaction times*. Reaction Time (mins) [C00056] [C00057] [C00058] [C00059] 5 0 0 99 1 15 0 0 90 10 30 4.0 0 60 36 60 5.2 0 40 54 150 7.1 1.8 13 78 210 7.9 2.1 3.5 86 300 9.3 2.4 0 88 *The reaction was quenched at the selected reaction time by addition of the aliquot of reaction solution to a water/ethyl acetate mixture.
The synthetic route of 5876-51-7 has been constantly updated, and we look forward to future research findings.