Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methylparaben | HCID 7456 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 5-Bromo-2-fluorobenzaldehyde | HCID 736327 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 59428082 | HCID 59428082 | 95.5% |
Reaction Steps
To a solution of 5-bromo-2-fluorobenzaldehyde (4.04 g, 20 mmol) (Alfa) in N,N-dimethylacetamide (30 mL) was added anhydrous K2CO3 (2.76 g, 20 mmol), and methyl 4-hydroxybenzoate (3.1 g, 20 mmol, Aldrich). The reaction mixture was heated at 170° C. for 1 h. The mixture was cooled to room temperature, diluted with ethyl acetate, washed with water, brine. The organic layer was separated, aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water, dried over MgSO4, concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:8 then 1:4) to give 4-(4-bromo-2-formyl-phenoxy)-benzoic acid methyl ester as a white solid (Yield 6.4 g, 95%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07776875B2 |
|---|
| Source dataset | uspto-grants-2010_08 |
|---|
| ORD ID | ord-0384146d4f6a435384594ee2b711aae2 |
|---|
| Source note | uspto-grants-2010_08 |
|---|