Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acrylic Acid | HCID 6581 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 3,5-Dibromoanisole | HCID 11021812 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | O-Xylene | HCID 7237 | — |
| Product | HCID 59443450 | HCID 59443450 | 32% |
Reaction Steps
To a solution of 1,3-dibromo-5-methoxybenzene (9.18 mmol, 1 eq) in 2 ml of xylene under a nitrogen atmosphere, acrylic acid (0.63 ml, 9.18 mmol, 1 eq), Pd(OAc)2 (1 mole %, 20.66 mg), triphenylphosphine (4 mole %, 69.2 mg) and triethylamine (19.278 ml, 2.7, 2.1 eq) are added. The reaction mixture is stirred at 100° C. for 11 h. Thereafter, 20 ml of water and 2 g of sodium carbonate were added, and the mixture was stirred at 100° C. for some minutes. The aqueous phase was subsequently separated and acidified. The precipitate that formed was dried and purified by means of column chromatography (eluent hexane/ethyl acetate 1/1) to obtain the desired product in a yield of 32% (751 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08546392B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-813684a0a6e24e379344dc472c2a5d94 |
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| Source note | uspto-grants-2013_10 |
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