O-Fluorobenzoyl chloride

Garcia et al. has extended the Batcho-Leimgruber procedure to the synthesis of 2-substituted indoles. Treatment of 36 with o-fluorobenzoyl chloride 37, followed by in situ hydrolysis and deformylation gave ketone 38. Reduction of nitroarylketone 38 with sodium hydrosulfite then furnished indole 39. Similarly, bromoacetylation of 36 gave an acylenamine which was converted into the phthalimido derivative 40. Hydrolysis and deformylation gave phthalimidoketone 41 which underwent reductive cyclization to furnish indole 42. 

Ferroglycine sulfate Ferrous fumarate Fluoranthene Flora ntyrone Fluoroacetyl chloride Afloqualone p-Fluorobenzaldehyde Sulindac Fluorobenzene Flubendazole o-Fluorobenzoyl chloride Flunitrazepam... 

Some pyrazole rings are electron-rich enough to undergo the Friedel-Crafts reaction. With the aid of AICI3 as the Lewis acid, the pyrazole below underwent the Friedel-Crafls aroylation widi o-fluorobenzoyl chloride to afford the ketone, an advanced intermediate for the synthesis of novel potential antipsychotic agents. ... 

N -o-Fluorobenzoyladenosine 5 -Phosphate. An aqueous solution of AMP (1.44 mmoles) is percolated through a column of Dowex 50 ion-exchange resin (pyridinium form, 20 ml). The eluate and aqueous washings are combined and evaporated under reduced pressure, and the residue is dried by repeated evaporation from it of pyridine (5 X 30 ml). To the residual oil is added pyridine (30 ml) and o-fluorobenzoyl chloride (30 mmoles), and the light yellow solution is stirred under anhydrous conditions in the dark. After 1.5 hr at room temperature it is poured into cold (<5°) water-chloroform (1 1, 200 ml) and the mixture is maintained at 0° for 15 min. The aqueous layer is washed with chloroform (2 X 30 ml), and the chloroform solutions are combined and evaporated. A solution of the residue in pyridine-water (2 1, 60 ml) is cooled in an ice bath. Aqueous 2 N NaOH (50 ml) at 0° is added, and the mixture is stirred in an ice bath for 4 min. Excess of pyridinium Dowex 50 is added to remove sodium ions, and the resin is removed by filtration and washed with water. The eluates are concentrated under reduced pressure to a gum which is extracted with anhydrous ether (5X50 ml). The residue is treated with anhydrous methanol (10 ml) and triethylamine (0.5 ml, 3.6 mmoles), and volatiles are removed under reduced pressure. The residue is dissolved in methanol (10 ml) with gentle warming, and... 

Preparation by demethylation of 2,3-dichloro-2 -fluoro-4-methoxybenzophenone (SM) with aluminium chloride in refluxing benzene for 5 h [476], (89%) [1031] or in refluxing methylene chloride overnight [475]. SM was obtained by Friedel-Crafts acylation of 2,3-dichloroanisole with o-fluorobenzoyl chloride in the presence of aluminium chloride in refluxing methylene chloride [475] or in ethylene dichloride for 2 h [476]. 

Preparation by Friedel-Crafts acylation of p-chloro-phenol with o-fluorobenzoyl chloride in the pres-C1 ence of aluminium chloride at 195° for 25 min (70%) [523]. 

Preparation by partial demethylation of 2-chloro-2 -fluoro-4,6-dimethoxy-benzophenone (SM) in ethylene dichloride in the presence of aluminium chloride at reflux (90°) for 3 h [476]. SM was obtained by reaction of o-fluorobenzoyl chloride with 5-chlororesorcinol dimethyl ether in methylene chloride in the presence of aluminium chloride at r.t. for 4 h [476]. 

Preparation by reaction of o-fluorobenzoyl chloride with 2-chlororesorcinol dimethyl ether in the presence of aluminium chloride in refluxing ethylene dichloride for 30 min [476], (67%) [1031]. 

Preparadon by Riedel-Crafts acylation of o-tert-butylphaiol with o-fluorobenzoyl chloride in ethylene dichloride in the presence of titanium tetrachloride, first at 0 , then at r.t. [816]. 

The reaction of o-fluorobenzoyl chloride with p-ketoesters in the presence of NaH has been proposed as a method for the synthesis of 2-methylchromone-3-carboxyUc acid and its esters. In particular, this reaction proved to be suitable for the preparation of ethyl 2-(trifluoromethyl)chromone-3-carboxylate (220) [110] (Scheme 71). 

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