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Contaminated with <2% of the 2-bromoxazole 9 and <0.2% of the 2,4-dibromo 10.
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Although the freezing point of DMF is -61 °C, the reaction mixture had a freezing point of < -70 °C.
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Quenching the reaction at -15 °C with NBS led to a ca. 2/1 ratio of regioisomers, favoring the C-4 product. NBS was added as a solution in DMF (2.7 mL/g of NBS) at room temperature. Pre-cooling of the NBS solution would be desirable, but it reduced the solubility significantly. More studies are needed to determine if the anion quench can be adapted in a flow reactor under non-cryogenic conditions.
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A trace amount (<1%) of the dibromide 10 was observed in the reaction but was purged during the isolation of 8.
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A trace amount (<1%) of the dibromide 10 was observed in the reaction but was purged during the isolation of 8.
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