7500-66-5

Usage

Uses

Used in Chemical Synthesis:
1-Benzoyl-1-bromocyclohexane is used as an intermediate in the synthesis of 1-Cyclohexenyl Phenyl Ketone (C992550), a useful reactant in the synthesis of cyclopentanone enol ethers. This application is particularly relevant in the pharmaceutical and chemical industries, where cyclopentanone enol ethers are utilized as key building blocks in the development of various pharmaceuticals and agrochemicals.

InChI:InChI=1/C13H15BrO/c14-13(9-5-2-6-10-13)12(15)11-7-3-1-4-8-11/h1,3-4,7-8H,2,5-6,9-10H2

Upstream product

• 712-50-5 Cyclohexyl phenyl ketone 
• 71-43-2 benzene 
• 2719-27-9 cyclohexanylcarbonyl chloride 

Downstream Products

• 1342886-83-2 C₁₃H₁₇BrO 
• 22612-69-7 1-phenylcyclohexane-1-carbaldehyde 
• 712-50-5 Cyclohexyl phenyl ketone 
• 135664-53-8 1-benzoylcyclohexane-1-carbonitrile 
• 106213-89-2 N-(cyclohex-1-en-1-yl)benzamide 
• 1069130-26-2 2-phenyl-2-(phenylethynyl)-1-oxaspiro[2.5]octane 
• 1070898-82-6 C₂₃H₃₄N₂O₅ 
• 7500-67-6 (1-benzoyloxy-cyclohexyl)-phenyl ketone 
• 947-19-3 1-hydroxycyclohexyl phenyl ketone 
• 92499-59-7 α-Hydroxycyclohexyl-phenyl-N-methylimin 
• 94381-96-1 phenyl-(1-piperidin-1-ylmethyl-cyclohexyl)-methanone 
• 1135-67-7 1-phenyl-cyclohexanecarboxylic acid 
• 15817-28-4 2-methoxy-2-phenyl-1-oxa-spiro[2.5]octane 

Relevant academic research and scientific papers

Access to α-Cyano Carbonyls Bearing a Quaternary Carbon Center by Reductive Cyanation

Reductive cyanation of tertiary alkyl bromides using electrophilic cyanating reagent and zinc reductant was developed, providing various α-cyano ketones, esters, and carboxamides containing a nitrile-bearing all-carbon quaternary center in good to excellent yields under mild reaction conditions. The corresponding reaction mechanism involving in situ generated organozinc reagent and reactivity distinction was elucidated by density functional theory computation.

A Highly Efficient Method for the Bromination of Alkenes, Alkynes and Ketones Using Dimethyl Sulfoxide and Oxalyl Bromide

The pairing of DMSO and oxalyl bromide is reported as a highly efficient brominating reagent for various alkenes, alkynes and ketones. This bromination approach demonstrates remarkable advantages, such as mild conditions, low cost, short reaction times, provides excellent yields in most cases and represents a very attractive alternative for the preparation of dibromides and α-bromoketones.

Iron-Catalyzed Acyl Migration of Tertiary α-Azidyl Ketones: Synthetic Approach toward Enamides and Isoquinolones

This paper reports that tertiary α-azidyl phenyl ketones can be transformed into enamides by treatment with FeBr2 at elevated temperature in DMF. The reaction proceeds via 1,2-benzoyl migration from α-carbon to the nitrogen atom, accompanied by expulsion of a nitrogen molecule. This protocol is suitable for the synthesis of N-(cyclopent-1-en-1-yl)benzamides, N-(cyclohex-1-en-1-yl)benzamides, and N-benzoyl-α-methyl enamines and provides a convenient approach toward isoquinolones.

Catalytic dehydrogenative dual functionalization of ethers: Dealkylation-oxidation-bromination accompanied by C-O bond cleavage: Via aerobic oxidation of bromide

Catalytic dehydrogenative dual functionalization (DDF) of ethers via oxidation, dealkylation, and α-bromination by the aerobic oxidation of bromide was developed to obtain the corresponding α-bromo ketones in high yields. In particular, the reaction of substituted tetrahydrofurans as cyclic ethers provided 3,3-dibromo tetrahydrofuran-2-ols in high yields selectively through the double α-bromination.

Stereoselective Traceless Borylation–Allenation of Propargylic Epoxides: Dual Role of the Copper Catalyst

Chiral α-allenols are prepared with high diastereocontrol through an unprecedented and spontaneous β-oxygen elimination of an α-epoxy vinyl boronate. Stochiometric experiments and DFT calculations support a dual role of the copper catalyst, which orchestrates the hydroboration and the syn-elimination step.

Building Congested Ketone: Substituted Hantzsch Ester and Nitrile as Alkylation Reagents in Photoredox Catalysis

For the first time, 4-alkyl Hantzsch esters were used to construct molecules with all-carbon quaternary centers by visible light-induced photoredox catalysis via transfer alkylation. Up to a 1500 h-1 turnover frequency was achieved in this reaction. Reactions of 4-alkyl Hantzsch nitriles as tertiary radical donors joined two contiguous all-carbon quaternary centers intermolecularly, and this chemistry was used to synthesize a common precursor of a class of hydroxysteroid dehydrogenase inhibitors.

Efficient bromination of olefins, alkynes, and ketones with dimethyl sulfoxide and hydrobromic acid

The oxidative bromination of olefins, alkynes, and ketones has been developed with HBr as the brominating reagent and DMSO as the mild oxidant. The simple conditions, high bromide-atom-economy, as well as easy accessibility and low cost of DMSO and HBr make the present strategy prospective for the synthesis of dibrominated alkanes, dibrominated alkenes and α-bromoketones.

An alternative reaction outcome in the gold-catalyzed rearrangement of 1-alkynyloxiranes

The gold(III)-catalyzed rearrangement of tetrasubstituted 1-alkynyloxiranes is described. This transformation led to a different reaction outcome with respect to related substrates previously studied. Thus, tertiary α-alkynylketones or alkynols can be selectively obtained. Moreover, gold(III) proved capable to catalyze the rearrangement of simple epoxides. These results indicate that gold(III) complexes act as oxophilic Lewis acids rather than π-acids in these transformations.

PROCESS FOR THE PREPARATION OF AROMATIC ALPHA-HYDROXY KETONES

Process for the preparation of aromatic alpha-hydroxyketones (aromatic α-hydroxyketones) that does not require the use of chlorine, sulfuryl chloride or bromine and comprises the halogenation of an intermediate aromatic ketone with a hydrogen halide in the presence of an oxidising compound.

CF3CO2ZnEt-mediated highly regioselective rearrangement of bromohydrins to aldehydes

A highly efficient and selective rearrangement reaction of bromohydrins to aldehydes mediated by CF3CO2ZnEt was described. The secondary and tertiary aldehydes were prepared under mild conditions in good to excellent yields (85-99%). The scope and limitations of this rearrangement process were also investigated.