Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 3-Fluorophenylboronic acid | HCID 2733986 | — |
| Reactant | methyl 4-(bromomethyl)-2-fluorobenzoate | HCID 18759821 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67974606 | HCID 67974606 | 52% |
Reaction Steps
Methyl 4-(bromomethyl)-2-fluorobenzoate (0.300 g; 1.21 mmol) was suspended in a mixture of water (1 mL) and 1,2-dimethoxyethane (3 mL) and 3-fluorophenylboronic acid (0.193 g; 1.34 mmol), tetrakis(triphenylphosphine)palladium(0) (0.071 g; 0.0061 mmol) and sodium carbonate (0.259 g; 2.43 mmol) were successively added. The resulting suspension was heated at 130° C. in a microwave oven for 20 minutes. The reaction mixture was diluted with ethyl acetate, and washed with water. The organic layer was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel (eluent 1 to 12% of ethyl acetate in heptane) to give 0.164 g (52%) of methyl 2-fluoro-4-(3-fluorobenzyl)benzoate as an oily residue.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09266832B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-5df814dfc0ac4891b4ec288ea199cb3b |
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| Source note | uspto-grants-2016_02 |
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