HuagongsheHuagongshe Chemistry Print Report · For research reference only
Bromide ion → Isohexane ethyl acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Bromide ion | HCID 259 | — |
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | [6s,9r,11r]2',3',4',5,5',6,7,8,9,10-Decahydro-2-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-5'-(2,2,2-trifluoroethyl)spiro[6,9-methanobenzocyclooctene-11,3'-[1,2,5]thiadiazole]1',1'-dioxide | HCID 23571079 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Isohexane ethyl acetate | HCID 21882781 | 50% |
Reaction Steps
A mixture of the bromide from Step 3 (0.075 g), the homochiral boronate ester from Example 24, Step 1 (0.105 g), tetrakis(triphenylphosphine) palladium (0) (0.1 g), 2M aqueous sodium carbonate (0.22 mL) and toluene (3 mL) was refluxed for 4 hours. The mixture was cooled, diluted with ethyl acetate (15 mL) and washed with water (10 ml). The organic phase was filtered through a Teflon membrane and concentrated. Flash column chromatography, eluting with 20% then 30% then 50% ethyl acetate-isohexane, gave the product as a yellow oil (0.085 g, 63%). MS (ES+) 628 ([MH]+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07041689B2 |
| Source dataset | uspto-grants-2006_05 |
| ORD ID | ord-3cdab137644142c58e92c006fb5139e5 |
| Source note | uspto-grants-2006_05 |