Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Ammonium Hydroxide | HCID 14923 | — |
| Reactant | HCID 17908432 | HCID 17908432 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Product | HCID 68671759 | HCID 68671759 | 20% |
Reaction Steps
A mixture of 1.37 g (4.17 mmol) of 1,3-dibromo-5-(methylsulfonylmethyl)benzene, 297 mg (2.53 mmol) of Zn(CN)2, and 298 mg (0.258 mmol) of Pd(PPh3)4 in 10 mL of DMF (degassed) was heated at 80° C. After 2.5 h, a 10% NH4OH aqueous solution was added, and the aqueous layer was extracted with EtOAc. The organic layer was washed with H2O and brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (50-60) % EtOAc/hexanes provided 228 mg of 3-bromo-5-(methylsulfonylmethyl)benzonitrile as a colorless solid in 20% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08299267B2 |
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| Source dataset | uspto-grants-2012_10 |
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| ORD ID | ord-42c3739ce6464fcd80050e2e1e78bb15 |
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| Source note | uspto-grants-2012_10 |
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