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Related Concept Videos

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

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Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
3.2K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

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An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
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β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

β-Dicarbonyl Compounds via Crossed Claisen Condensations

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Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds.  The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
3.4K
Halogenation of Alkenes02:46

Halogenation of Alkenes

16.8K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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A One-Step Synthesis of β-Bromocodide from Codeine.

Christopher W Cunningham1, Jeffrey R Deschamps2, Andrew Coop3

  • 1Department of Pharmaceutical Science, Concordia University Wisconsin School of Pharmacy, 12800 N. Lake Shore Drive, PH 239, Mequon, WI 53097, USA.

Journal of Pharmaceutical Sciences and Pharmacology
|September 29, 2021
PubMed
Summary
This summary is machine-generated.

Researchers discovered a new, single-step synthesis for β-bromocodide, a key intermediate in developing novel opioid analgesics. This finding offers a more efficient route to potential pain management therapies.

Keywords:
Boron Tribromide (BBr3)CodeineMorphineX-Ray Crystallographyβ-Bromocodide

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Pharmacology

Background:

  • Opioid analgesics are crucial for managing severe chronic pain.
  • Developing new opioid derivatives aims to improve therapeutic profiles.
  • Traditional synthesis routes can be complex and inefficient.

Purpose of the Study:

  • To report the first single-step synthesis of β-bromocodide.
  • To identify a novel SN2' substitution product during codeine modification.
  • To establish β-bromocodide as a valuable intermediate for C-6-demethoxythebaine derivatives.

Main Methods:

  • Attempted 3-O-demethylation of codeine using boron tribromide (BBr3).
  • Characterization of the reaction product using Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Confirmation of the product's structure via X-ray crystallography.

Main Results:

  • An unanticipated SN2' substitution reaction occurred, yielding β-bromocodide.
  • NMR and X-ray crystallographic data confirmed the structure of β-bromocodide.
  • The synthesis provides a direct, single-step route to this important intermediate.

Conclusions:

  • The study presents the first reported single-step synthesis of β-bromocodide.
  • β-bromocodide is a valuable intermediate for synthesizing C-6-demethoxythebaine derivatives.
  • This efficient synthesis could facilitate the development of new opioid-based analgesics.