Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzoic acid, 2-iodo-, methyl ester | HCID 69132 | — |
| Reactant | Benzene, 1-bromo-4-ethynyl- | HCID 136603 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 14088833 | HCID 14088833 | — |
Reaction Steps
To a solution of 2-iodo-benzoic acid methyl ester (1.31 g, 5.00 mmol) in DMF (10 ml) are added bis(triphenylphosphine)-palladium(II)-chloride (351 mg, 0.50 mmol), copper(I) iodide (28.5 mg, 0.15 mmol), triethylamine (2.08 ml, 15.0 mmol) and 1-bromo-4-ethynyl-benzene (905 mg, 5.00 mmol). The resulting dark brown solution is flushed with nitrogen, heated to 80° C. and stirred in a closed reaction vial at this temperature for 16 hours. The reaction mixture is allowed to cool to room temperature and partitioned between water and dichloromethane. The organic phase is washed with 1 N HCl, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to give 2-(4-bromo-phenylethynyl)-benzoic acid methyl ester as brown oil; HPLC/MS 3.46 min (B), [M+H] 315/317.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09376433B2 |
|---|
| Source dataset | uspto-grants-2016_06 |
|---|
| ORD ID | ord-71ec6d75f1c2421c9a10f84bb7761851 |
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| Source note | uspto-grants-2016_06 |
|---|
