Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Cyanide | HCID 8929 | — |
| Reactant | Benzoic acid, 3-(bromomethyl)-2-chloro-, methyl ester | HCID 57386060 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57386575 | HCID 57386575 | 79% |
Reaction Steps
To a solution of methyl 3-(bromomethyl)-2-chlorobenzoate (748 mg, 2.84 mmol) in N,N-dimethylformamide (7 mL) was added sodium cyanide (412 mg, 8.41 mmol), and the mixture was stirred under a nitrogen stream at 80° C. for 1 hr. The reaction mixture was diluted with a mixed solvent of ethyl acetate and hexane (1:1). The solution was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=98/2→80/20) and crystallized from ethyl acetate/hexane to give the title compound (470 mg, 79%) as white crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08324395B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-c26f01914bba40f6afd375405423e8a9 |
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| Source note | uspto-grants-2012_12 |
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