HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1644720Generated: October 25, 2026
Triethylamine → 4-Fluoro-2-(4-methanesulfonyl-phenylethynyl)-benzaldehyde
https://huagongshe.com/reaction/1644720
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Bromo-4-fluorobenzaldehyde | HCID 2773319 | — |
| Reactant | 1-Ethynyl-4-(methanesulfonyl)benzene | HCID 22042612 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-Fluoro-2-(4-methanesulfonyl-phenylethynyl)-benzaldehyde | HCID 59350830 | 79.2% |
Reaction Steps
A degassed mixture of 1-ethynyl-4-methanesulfonyl-benzene (2.5 g, 13.87 mmol), bis(triphenylphosphine)palladium(II) chloride (0.49 g, 0.69 mmol), copper(I) iodide (0.13 g, 0.69 mmol), triethylamine (28 mL), and 2-bromo-4-fluorobenzaldehyde (3.38 g, 16 mmol) in dichloromethane (10 mL) was stirred at 80° C. for 3.5 hours, then at room temperature overnight. The reaction mixture was partitioned between dichloromethane and water. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (RediSep® Flash column, 230-400 mesh, 15-35% ethyl acetate in hexane) gave 4-fluoro-2-(4-methanesulfonyl-phenylethynyl)-benzaldehyde (3.32 g, 79%). MS (ESI+) cald. for C16H11FO3S [(M+H)+] 302, obsd. 302.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08124629B2 |
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| Source dataset | uspto-grants-2012_02 |
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| ORD ID | ord-5476d957c5804cba8b67c683dddda991 |
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| Source note | uspto-grants-2012_02 |
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