Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium methanethiolate | HCID 4378561 | — |
| Reactant | HCID 66681707 | HCID 66681707 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 66682427 | HCID 66682427 | 95% |
Reaction Steps
1-Bromo-3-methoxy-5-[(1S)-2-methoxy-1-methylethoxy]benzene (9.21 g, 33.5 mmol) synthesized in Example (38a) was dissolved in 1-methyl-2-pyrrolidone (100 mL), and sodium thiomethoxide (2.75 g, 37.3 mmol) was added, followed by stirring at 130° C. for 3 for hours under nitrogen atmosphere. The reaction solution was cooled to room temperature, 2N hydrochloric acid (500 mL) was added, and extraction was carried out with diethyl ether (300 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=20%-25%) to afford the desired compound (8.30 g, yield 95%) as a colorless liquid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08415359B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-5aef0ab5c8104430bde3b2b7eb4e344b |
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| Source note | uspto-grants-2013_04 |
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