Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1-Bromo-2,4,5-trifluorobenzene | HCID 67597 | — |
| Reactant | (+)-Epichlorohydrin | HCID 149428 | — |
| Reactant | HCID 178418918 | HCID 178418918 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 54764462 | HCID 54764462 | — |
Reaction Steps
84.4 g of 1-bromo-2,4,5-trifluorobenzene and 42.1 mL of tetrahydrofuran were added to 250 mL flask, and the resulting reaction solution was cooled to −15-20° C. Under nitrogen atmosphere, 20 mL of isopropylmagnesium chloride [2.0 M tetrahydrofuran solution] was dropped to the reaction solution, and stirred at 0-5° C. for 2 hours to produce Grinard reagent. 31.6 mL of (S)-epichlorohydrin and 42.1 mL of tetrahydrofuran were added to another 250 mL flask; the resulting reaction solution was cooled to −15-−20° C.; and then 7.6 g of copper iodide was added thereto. 42.1 mL of the Grinard reagent produced under nitrogen atmosphere was dropped, and stirred for 3 hours while the reaction temperature was maintained at −15-−20° C. 297 mL of 2 N hydrochloric acid aqueous solution that was cooled at 0-5° C. was dropped to the reaction solution, and then extracted with 297 mL of isopropylether. An organic layer was dehydrated with sodium sulfate, and then concentrated under reduced pressure to obtain 89.8 g of a title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09249109B2 |
|---|
| Source dataset | uspto-grants-2016_02 |
|---|
| ORD ID | ord-a22620c3812a490c9c65b8a5c8c6fd98 |
|---|
| Source note | uspto-grants-2016_02 |
|---|