HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 405801Generated: October 30, 2026
5-Bromo-4-fluoro-2-methylaniline → 5-Amino-2-fluoro-4-methylbenzonitrile
https://huagongshe.com/reaction/405801
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 5-Bromo-4-fluoro-2-methylaniline | HCID 2782786 | — |
| Reactant | HCID 178418546 | HCID 178418546 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | 5-Amino-2-fluoro-4-methylbenzonitrile | HCID 86677449 | 36% |
Reaction Steps
A mixture of 5-bromo-4-fluoro-2-methylaniline (2.04 g, 10.0 mmol), CuCN (889 mg, 10.0 mmol) and CuI (1.9 g, 10.0 mmol) in NMP was purged with N2 for 5 minutes and then sealed and heated at 195° C. for 30 minutes under microwave condition. The mixture was subjected to standard aqueous workup to give a residue which was purified by silica chromatography to yield 5-amino-2-fluoro-4-methylbenzonitrile (51) (540 mg, 36% yield). MS m/z 151.0 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08754071B2 |
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| Source dataset | uspto-grants-2014_06 |
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| ORD ID | ord-b2064c9d8a294fa5b052e6e3f4e86f91 |
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| Source note | uspto-grants-2014_06 |
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