Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Bromine | HCID 24408 | — |
| Reactant | Trimethylsilyl triflate | HCID 65367 | — |
| Reactant | HCID 54468657 | HCID 54468657 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 54201425 | HCID 54201425 | 97% |
Reaction Steps
To an ice-cooled solution of allyl 2-diazo-3-ketopentanoate (9.1 g, 0.05 mole) in 100 mL of CH2CL2, was added 8.35 mL of triethylamine, followed by dropwise addition of 11.6 mL trimethylsilyl triflate (13.34 g, 0.06 mole) over twenty minutes. The resulting solution (orange) was stirred at 0° C. for one hour. A solution of bromine (8.0 g, 0.05 mole) in 30 mL CH2Cl2 was added over twenty minutes at 0° C. The mixture was stirred at 0° C. for one hour. The reaction mixture was then washed with water three times, dried over magnesium sulphate and concentrated to give the title compound as an oil (12.74 G, 97% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04841043 |
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| Source dataset | uspto-grants-1989_06 |
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| ORD ID | ord-266acb3ee4c840548dc9022b61792d0f |
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| Source note | uspto-grants-1989_06 |
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