Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | 1,1'-(Azodicarbonyl)dipiperidine | HCID 73042 | — |
| Reactant | Methyl 4-fluorosalicylate | HCID 2775386 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58575556 | HCID 58575556 | — |
Reaction Steps
To a solution of 2 g of methyl 4-fluoro-2-hydroxybenzoate in 60 mL of tetrahydrofuran were added 1.83 g of hydroxyethyl 2-acetate and 3.56 g of tributylphosphine, and then 5.93 g of 1,1′-(azodicarbonyl)dipiperidine was slowly added thereto under ice-cooling, followed by stirring for 20 minutes. The mixture was warmed to room temperature and stirred for 6 hours. The reaction mixture was poured into a mixed liquid of water and ethyl acetate. The aqueous layer was separated, the organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate) to obtain 2.4 g of methyl 2-(2-acetoxyethoxy)-4-fluorobenzoate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08674096B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-0008cf0559a44d2ea39f3dddaad93da5 |
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| Source note | uspto-grants-2014_03 |
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