Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1-Bromo-4-iodobenzene | HCID 11522 | — |
| Reactant | (3S)-pyrrolidin-3-ol | HCID 2733874 | — |
| Reactant | Potassium phosphate, tribasic, monohydrate | HCID 22031701 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | 2-(Dimethylamino)ethanol | HCID 7902 | — |
| Product | HCID 67148437 | HCID 67148437 | 84.2% |
Reaction Steps
A mixture of 1-bromo-4-iodo-benzene (50.0 g, 177 mmol), (S)-pyrrolidin-3-ol (28.6 mL, 353 mmol), CuI (6.73 g, 35.3 mmol) and K3PO4.H2O (81.4 g, 353 mmol) in N,N-dimethylaminoethanol (177 mL) was stirred at 55° C. for 60 h. The mixture was allowed to cool to rt, and water was added. The mixture was extracted several times with CH2Cl2. The combined org. extracts were washed with a 1:1 mixture of aq. conc. NH3 and water. The NH3-containing aq. layer was extracted with CH2Cl2. The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Crystallization of the crude from EtOAc/heptane yielded the title compound (36.1 g, 84%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07968720B2 |
|---|
| Source dataset | uspto-grants-2011_06 |
|---|
| ORD ID | ord-faaf1c244e6943e08862af7f82e1e3ed |
|---|
| Source note | uspto-grants-2011_06 |
|---|
