HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → Tert-butyl 3-fluoro-4-iodophenylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 2,5-Diiodofluorobenzene | HCID 2737096 | — |
| Reactant | Tert-butylcarbamate | HCID 21252905 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Tert-butyl 3-fluoro-4-iodophenylcarbamate | HCID 44203004 | 531% |
Reaction Steps
A mixture of 2,5-diiodofluorobenzene (1.36 g, 3.90 mmol), tert-butylcarbamate (0.454 g, 3.88 mmol), xantphos (0.233 g, 0.40 mmol) and Cs2CO3 (dry powder, 2.48 g, 7.61 mmol) in THF (12 mL) was degassed with Ar before being charged with Pd2(dba)3 (0.071 g, 0.078 mmol). It was stirred at 75 C overnight. After being cooled to room temperature, water and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was loaded to a flash column, eluted with 0-10% EtOAc in hexane to give tert-butyl 3-fluoro-4-iodophenylcarbamate (716 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08318755B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-d509df1fa1ea4359a602f2d45b6a9ee3 |
| Source note | uspto-grants-2012_11 |