Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 54450619 | HCID 54450619 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 19079050 | HCID 19079050 | 86.4% |
Reaction Steps
Dissolved 2-[6,11-dihydro-dibenz[b,e]oxepin-11-ylidene]-ethanol (10.90 g, 0.0457 mol) in 175 mL of dichloromethane. Added ethanol (21.07 g, 26.8 mL, 0.457 mol), and cooled to 0° C. under a nitrogen atmosphere. Added N-bromosuccinimide (8.96 g, 0.0503 mol) portionwise. Warmed slowly to room temperature over 60 mins. Added 200 mL of saturated NaHCO3, and separated layers. Extracted aqueous solution with dichloromethane. Dried combined organic extracts with MgSO4, filtered, and evaporated. Purified crude product by flash chromatography on silica gel eluting with 1:4 ethyl acetate:hexane. Combined appropriate fractions, and evaporated to give 14.35 g (86% yield) of 2-bromo-2-[6,11-dihydro-11-ethoxy-dibenz[b,e]oxepin-11-yl]-ethanol as a light yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05538986 |
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| Source dataset | uspto-grants-1996_07 |
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| ORD ID | ord-19e7384e58b543a9997cb5ec888fa85d |
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| Source note | uspto-grants-1996_07 |
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