Bromine → HCID 59278516, compound

To a solution of methyl 1H-pyrrolecarboxylate (4.00 g, 32.00 mmol) in dioxane was added anhydrous sodium acetate (4.92 g, 60.00 mmol) followed by a solution of bromine (32.00 mmol) in dioxane (150 mL) dropwise. After 4 hours, the solvent was concentrated in vacuo and the residue was poured into an ice cold solution of 5% aqueous sodium carbonate (100 mL) and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 10-40% ethyl acetate in heptane. The major fractions were combined and the solvent was concentrated in vacuo to afford the title compound.

1. concentrationthe solvent was concentrated in vacuo
2. additionthe residue was poured into an ice cold solution of 5% aqueous sodium carbonate (100 mL)
3. extractionextracted with ethyl acetate
4. washThe combined organic layers were washed with brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in vacuo
7. customThe residue was purified by silica gel chromatography
8. washeluting with 10-40% ethyl acetate in heptane
9. concentrationthe solvent was concentrated in vacuo

ORD record

ord-38b6a40ea149412db626dc3f3210fd62

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08338610B2