HuagongsheHuagongshe Chemistry Print Report · For research reference only
Iodine → Tert-butyl 3-(3-chloro-5-fluorophenyl)-3-hydroxypyrrolidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Iodine | HCID 807 | — |
| Reactant | Tert-butyl 3-oxopyrrolidine-1-carboxylate | HCID 471360 | — |
| Reactant | 1-Bromo-3-chloro-5-fluorobenzene | HCID 2736223 | — |
| Reactant | Magnesium | HCID 5462224 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Tert-butyl 3-(3-chloro-5-fluorophenyl)-3-hydroxypyrrolidine-1-carboxylate | HCID 67402932 | 28% |
Reaction Steps
Preparation according to Preparation 1. 1-Bromo-3-chloro-5-fluorobenzene (5 g, 23.9 mmol) in dry tetrahydrofuran (100 ml), magnesium turnings (0.57 g, 23.9 mmol) and one crystal of iodine. 1-N-boc-3-pyrrolidone (4.41 g, 23.9 mmol) in dry tetrahydrofuran (50 ml). The crude product was purified by flash column chromatography on silica gel (ethyl acetate/isooctane, 1:9 to 1:1) gave the title compound (2.1 g, 28%). MS m/z (rel. intensity, 70 eV) 259 (45), 214 (69), 184 (35), 143 (37), 57 (bp).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09035073B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-0f0c236c7c4a4c78b20856e3d01338b0 |
| Source note | uspto-grants-2015_05 |