572-84-9

Usage

InChI:InChI=1/C14H7FO2/c15-8-5-6-11-12(7-8)14(17)10-4-2-1-3-9(10)13(11)16/h1-7H

Upstream product

• 57271-91-7 N-butyl-2-hydroxybenzamide 
• 119-36-8 methyl salicylate 
• 1242436-38-9 9,10-dioxo-9,10-dihydroanthracen-2-yl trifluoromethanesulfonate 
• 117-79-3 2-aminoanthraquinone 
• 7664-93-9 sulfuric acid 
• 7649-92-5 2-(4-fluorobenzoyl)benzoic acid 
• 381-61-3 fluoroprene 
• 130-15-4 [1,4]naphthoquinone 
• 46871-20-9 2-diazoanthraquinone 
• 362-17-4 3-fluoro-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid 
• 131-09-9 2-chloroanthracene-9,10-dione 
• 523-17-1 2-fluoro-3-methylanthraquinone 

Downstream Products

• 494800-47-4 1-[9'-(2'-fluoroanthryl)]-2,2-dimesitylvinyl acetate 
• 494800-45-2 1-[9'-(2'-fluoroanthryl)]-2,2-dimesitylethenol 
• 21454-60-4 2-Fluoroanthracene 

Relevant academic research and scientific papers

Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy- N-Butylbenzamides

The N-butyl amide group, CONHBu, has been found to be an effective promoter of the [1,2]-Wittig rearrangement of aryl benzyl ethers and thus allow the two-step synthesis of isomerically pure substituted diarylmethanols starting from simple hydroxybenzoic acid derivatives. The method is compatible with a wide range of functional groups including methyl, methoxy, and fluoro, although not with nitro and, unexpectedly, is applicable to meta as well as ortho and para isomeric series.

A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides

A new biaryl monophosphine ligand (AlPhos, L1) allows for the room-temperature Pd-catalyzed fluorination of a variety of activated (hetero)aryl triflates. Furthermore, aryl triflates and bromides that are prone to give mixtures of regioisomeric aryl fluorides with Pd-catalysis can now be converted to the desired aryl fluorides with high regioselectivity. Analysis of the solid-state structures of several Pd(II) complexes, as well as density functional theory (DFT) calculations, shed light on the origin of the enhanced reactivity observed with L1.

Stable simple enols. Resolution of chiral 1-[9′-(2′-fluoroanthryl)]-2,2-dimesitylethenol. A different racemization mechanism for the enol and its acetate

Chiral 1-[9′-(2′-methoxyanthryl)]-2,2-dimesitylethenol (2), 1-[9′-(2′-fluoroanthryl)]-2,2-dimesitylethenol (3), and 1-[9′-(2′-fluoroanthryl)]-2,2-dimesitylvinyl acetate (4) were synthesized and their DNMR behavior in C6D5NO2 was studied. 3 and 4 were resolved on an amylose tris(3,5-dimethylphenylcarbamate) HPLC column to their enantiomers. Acetate 4 racemizes slowly in solution with ΔGe?, ΔHe?, and ΔSe? values of 26.2, 27.6 kcal mol-1, and 4.3 eu, respectively, as expected for a rotational ββ′-2-ring flip process in a vinyl propeller and the racemization is unaffected by added TFA, Et3N, and EtOD. Although 3 racemizes almost 350 times faster, the racemization is catalyzed by TFA and shows bell-shape catalysis by Et3N and a KIE in a partially deuteriated solvent. From this and the DNMR data, it is concluded that 3 does not racemize via a rotational ββ′-2-ring flip. Five nonflip routes are discussed for the racemization of 3, and it is concluded that only the one initiated by protonation at C1 does not contradict the experimental data. By analogy with the E/Z isomerization of the structurally related 2-(m-methoxymesityl)-1,2-dimesitylethenol 17, it is suggested that in the absence of added catalyst one or more enol molecule(s) catalyze the enantiomerization of another one. Only partial resolution was achieved for 2 and from the similarity of its behavior with that of 3, it is suggested that it racemizes by the same mechanism.

Products of the condensation reaction of 2-(4-fluorobenzoyl)benzoic acid with m-cresol

The preparation and structural elucidation of the new isomeric 3-(4-fluorophenyl)-3-(hydroxymethyl)phthalides made from m-cresol and 2-(4-fluorobenzoyl)benzoic acid are described.