Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | HCID 66683402 | HCID 66683402 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66681701 | HCID 66681701 | 94% |
Reaction Steps
t-Butyl 2-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-1-carboxylate (2.70 g, 5.38 mmol) synthesized in Example (13b) was dissolved in tetrahydrofuran (50 mL), and cooled to 0° C. After addition of N-bromosuccinimide (960 mg, 5.38 mmol) with stirring under nitrogen atmosphere, stirring was carried out at room temperature for 4 hours. Water (50 mL) was added, and extraction was carried out with ethyl acetate (50 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=20%-40%) to afford the desired compound (2.93 g, yield 94%) as a brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08415359B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-f17e806f9a4d477db87372bb2ae134e6 |
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| Source note | uspto-grants-2013_04 |
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