Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Bromoresorcinol | HCID 81105 | — |
| Reactant | 2-Fluoro-5-methoxyphenylboronic acid | HCID 4157211 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1-Butanol | HCID 263 | — |
| Product | HCID 117759897 | HCID 117759897 | 84.7% |
Reaction Steps
Under a nitrogen atmosphere, to a solution of 4-bromoresorcinol (10.1 g) in 1-butanol (200 mL) were added 2-fluoro-5-methoxyphenylboronic acid (10.8 g), tetrakis(triphenylphosphine)palladium(0) (3.00 g) and 2.0 M aqueous sodium carbonate solution (54 mL), and the mixture was stirred at 90° C. for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (10.6 g) as a pale-yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09382188B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-09b0ad0715a54e1280b250d33050fc02 |
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| Source note | uspto-grants-2016_07 |
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