Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 4-Bromoaniline | HCID 7807 | — |
| Reactant | Ethyl orthoformate | HCID 31214 | — |
| Reactant | 3-Cyclopropyl-3-Oxopropionic Acid Methyl Ester | HCID 10130016 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178500750 | HCID 178500750 | 58% |
Reaction Steps
A stirred mixture of methyl 3-cyclopropyl-3-oxopropanoate (20 g, 0.141 mol), triethyl orthoformate (28 mL, 0.169 mol), and 4-bromoaniline (24.2 g, 0.141 mol) were heated at 130° C. for 5 h with a Dean Stark trap. After this time the reaction was cooled to room temperature, diluted with methylene chloride and filtered through a pad of silica. The filtrate was concentrated to afford the desired product (26.5 g, 55%) as a yellow solid: ESI MS m/z 324 [C14H14BrNO2+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09120749B2 |
|---|
| Source dataset | uspto-grants-2015_09 |
|---|
| ORD ID | ord-140f38c1fde84ab99043527ca64ad70d |
|---|
| Source note | uspto-grants-2015_09 |
|---|
