Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-Bromo-3,5-dimethylphenol | HCID 81970 | — |
| Reactant | HCID 11320954 | HCID 11320954 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 86697164 | HCID 86697164 | — |
Reaction Steps
2-Thia-1-aza-bicyclo[3.1.0]hexane 2,2-dioxide (Liang, Jiang-Lin et al., Organic Letters, 2002, vol. 4, #25 p. 4507-4510) (300 mg) is added to a suspension of 4-bromo-3,5-dimethylphenol (1.14 g) and sodium hydride (140 mg of a 60% mineral oil suspension) in 25 mL of N,N-dimethylacetamide. The reaction mixture is stirred at 130° C. for 5 h. Water is added and the reaction mixture is extracted with ethyl acetate. The organic phase is separated, dried over sodium sulfate and concentrated under vacuum. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0→30:70) to give the title compound. Yield: 220 mg.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08642585B2 |
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| Source dataset | uspto-grants-2014_02 |
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| ORD ID | ord-b41520d52b054581b015a9d18235363e |
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| Source note | uspto-grants-2014_02 |
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