Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 3-Bromophenol | HCID 11563 | — |
| Reactant | Epibromohydrin | HCID 18430 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-[(3-Bromophenoxy)methyl]oxirane | HCID 3865342 | 113.3% |
Reaction Steps
To a solution of compound NaH (416.2 mg, 17.34 mmol) in DMF (10 mL) was added 3-bromophenol (1.0 g, 5.78 mmol) at 20° C. After addition the solution was stirred for 5 minutes at this temperature before the addition of 2-(bromomethyl)oxirane (1.2 g, 8.67 mmol). The reaction mixture was stirred for 16 h at 20° C. Once complete the reaction mixture was treated with water (50 mL) and extracted with EA (2×20 mL) and the organic layers combined and washed with NaHCO3, brine (30 mL), dried over Na2SO4 and concentrated to give the compound 2-((3-bromophenoxy)methyl)oxirane (1.5 g, crude) as colorless oil which was used in next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08906900B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-c36ef686203b46e098d17c307c600010 |
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| Source note | uspto-grants-2014_12 |
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