Related Experiment Video
Updated: Jun 3, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Efficient synthesis of 17-acetyl-13-(p-bromophenyl)-3-methoxy-11,11-bis(methoxycarbonyl)gona-1,3,5(10)-trienes
Nicolas Galy1, Maurice Santelli
1Laboratoire Chimie Provence, UMR CNRS 6264, Faculté des Sciences et Techniques de Saint-Jérôme, Avenue Escadrille Normandie-Niémen, 13397 Marseille Cedex 20, France.
Abstract:
We described an efficient synthesis of (8β,9β,14β)-17β-acetyl-13β-p-bromophenyl-11,11-di(methoxycarbonyl)-3-methoxygona-1,3,5(10)-triene, (8β,9α,14β)-17β-acetyl-13β-p-bromophenyl-11,11-di(methoxycarbonyl)-3-methoxygona-1,3,5(10)-triene, (8β,9β,14β)-13 β-p-bromophenyl-11,11-di(methoxycarbonyl)-17β-(2-hydroxyethyl)-3-methoxygona-1,3,5(10)-triene, and (8β,9β,14β)-13β-p-bromophenyl-11,11-di(methoxycarbonyl)-17β-(2-oxoxyethyl)-3-methoxygona-1,3,5(10)-triene in five or six steps from 1-iodo-4-methoxybenzocyclobutene and readily available materials.
Related Concept Videos
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

