Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Benzoyl chloride | HCID 7412 | — |
| Reactant | Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoate | HCID 53395349 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 67905085 | HCID 67905085 | 29% |
Reaction Steps
A solution of 5 g (17.5 mmol) of methyl α-(2-bromomethylphenyl)-β-methoxyacrylate and 2.5 g (17.8 mmol) of benzoyl chloride in 50 ml of dimethoxyethane is added dropwise to 2.3 g (0.035 mol) of zinc powder and 600 mg (0.9 mmol) of Pd(Ph3P)2Cl2 under nitrogen and the mixture is then heated at 50° C. for 30 minutes. Water is added, the mixture is extracted with ethyl acetate and the organic phase is dried and evaporated down. The residue is chromatographed over silica gel using hexane/ethyl acetate. 1.6 g of compound No. 1 (Table 1) are obtained as a pale yellow solid of melting point 97°-99° C. Yield: 29%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05147892 |
|---|
| Source dataset | uspto-grants-1992_09 |
|---|
| ORD ID | ord-be2fb03c597d4540aa0057fab5459fa4 |
|---|
| Source note | uspto-grants-1992_09 |
|---|