Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl | HCID 2734217 | — |
| Reactant | 4-Bromo-5-fluoro-2-methoxyaniline | HCID 22347298 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 71743885 | HCID 71743885 | 492.4% |
Reaction Steps
To a pressure tube was added 4-bromo-5-fluoro-2-methoxyaniline (0.24 g, 1.1 mmol), zinc cyanide (0.10 g, 0.87 mmol), Pd2(dba)3 (100 mg, 0.11 mmol), DavePhos (86 mg, 0.22 mmol) and DMF (3 mL). The reaction was sealed and stirred at 100° C. for 6 hours. The reaction was diluted with water and extracted with EtOAc. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography to give 4-amino-2-fluoro-5-methoxybenzonitrile (0.18 g, 77%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09145402B2 |
|---|
| Source dataset | uspto-grants-2015_09 |
|---|
| ORD ID | ord-4af533ec264f451b83bc778ff4333a2e |
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| Source note | uspto-grants-2015_09 |
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