HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2069078Generated: October 31, 2026
Dimethyl Sulfoxide → 2-(3-Bromo-5-methoxyphenyl)acetonitrile
https://huagongshe.com/reaction/2069078
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethyl Sulfoxide | HCID 679 | — |
| Reactant | Sodium Cyanide | HCID 8929 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1-Bromo-3-(bromomethyl)-5-methoxybenzene | HCID 12276449 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 2-(3-Bromo-5-methoxyphenyl)acetonitrile | HCID 21242965 | 86.4% |
Reaction Steps
Sodium cyanide (3.4 g; WAKO) was added to a DMSO (100 mL) solution of Intermediate 2 (16.3 g) at room temperature and the resulting mixture was stirred at 40° C. for 1 hour and 40 minutes. Ethyl acetate (300 mL) and saturated aqueous sodium bicarbonate solution (150 mL), and water (150 mL) were added to extract the reaction mixture, the reaction mixture was washed with saturated brine (300 mL), the organic layer was dried, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Yamazen; n-hexane/ethyl acetate) to give the title compound (11.37 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08299055B2 |
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| Source dataset | uspto-grants-2012_10 |
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| ORD ID | ord-403b95ede2c1470c813392e81959ab6c |
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| Source note | uspto-grants-2012_10 |
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