Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzyl Alcohol | HCID 244 | — |
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | 5-Bromo-6-chloropyridine-3-carboxylic acid | HCID 285433 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 21109715 | HCID 21109715 | 23.6% |
Reaction Steps
A suspension of 5-bromo-6-chloro-nicotinic acid (CAS [29241-62-1], 1 g), benzylalcohol (0.686 g) and KOH (1.104 g) in DMSO (4 ml) was stirred at 140° C. for 15 min. DMSO (2 ml) was added and the mixture was stirred at 140° C. for 30 min. The mixture was cooled to room temperature. Ice was added and the mixture was acidified using 1 M HCl. The mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried, filtered and concentrated. The product was purified by flash chromatography (SiO2, CH2Cl2=>CH2Cl2/MeOH 4:1) to give 6-benzyloxy-5-bromo-nicotinic acid (0.308 g) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07229999B2 |
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| Source dataset | uspto-grants-2007_06 |
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| ORD ID | ord-0eb31a1a897d4e2fbf8e399e11d5b7c8 |
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| Source note | uspto-grants-2007_06 |
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