HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1945307Generated: October 30, 2026
4-Bromo-5-fluoro-2-[(trimethylsilyl)ethynyl]aniline → 5-bromo-6-fluoro-1H-indole
https://huagongshe.com/reaction/1945307
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 4-Bromo-5-fluoro-2-[(trimethylsilyl)ethynyl]aniline | HCID 68494805 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-bromo-6-fluoro-1H-indole | HCID 11687145 | — |
Reaction Steps
CuI (0.932 g, 4.89 mmol) was added to a solution of 4-bromo-5-fluoro-2-[(trimethylsilyl)ethynyl]aniline (0.700 g, 2.45 mmol) in DMF (25 mL). The resulting suspension was heated at 100° C. for 1 h. The reaction mixture was partitioned between 10% aqueous Na2S2O3 and Et2O. The aqueous layer was extracted with Et2O. The combined organic layers were washed with 5 N aqueous NaOH and brine, dried (Na2SO4), filtered, and concentrated. The crude product was used in the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08394969B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-5b65f64e3bef4c829e140ff6ee7d89d1 |
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| Source note | uspto-grants-2013_03 |
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