2- Nitrobenzophenone Nitrobenzoyl chloride

Nitrobenzophenone, 32, 12 o-Nitrobenzoyl chloride, 30, 70 o-Nitrochlorobenzene, 32, 24 9-Nitro-10-chloro-9,10-dihydroanthra-... 

To a stirred and cooled (ice bath) suspension of 25 parts of aluminum chloride in 52 parts of fluorobenzene is added dropwise a solution of 27.5 parts of 4-chloro-3-nitrobenzoyl chloride in 52 parts of fluorobenzene. Upon completion, stirring is continued overnight at room temperature. The reaction mixture is poured onto water and the product is extracted with methylene chloride. The extract is washed successively with sodium hydrogen carbonate solution and water, dried, filtered and evaporated in vacuo. The solid residue is crystallized from 2-propanol, yielding 4-chloro-4 -fluoro-3-nitrobenzophenone MP 97.9°C. 

Preparation by Friedel-Crafts acylation of bromobenzene with m-nitrobenzoyl chloride, reduction of the obtained 4-bromo-3 -nitrobenzophenone and diazotization of the resulting 3-amino-4 -bromobenzophenone, followed by hydrolysis of the diazonium salt [900]. 

Also obtained by reaction of m-nitrobenzoyl chloride with anisole in the presence of aluminium chloride in refluxing carbon disulfide for 2 h (16%) [959], In this reaction, 4-methoxy-3 -nitrobenzophenone was the major product. 

Preparation by acylation of phenetole with m-nitrobenzoyl chloride in ethyl ether in the presence of alumininm chloride, then dealkylation of the 4-ethoxy-3 -nitrobenzophenone so formed with the same catalyst [141], in boiling carbon disulfide (60-70°) for 8 h [619] according to [139]. Preparation by Fries rearrangement of phenyl m-nitrobenzoate with alumininm chloride [897] without solvent at 120° or at 160° for 2 h (32%) [958]. 

Preparation by deethylation of 2-ethoxy-5-methyl-4 -nitrobenzophenone (SM) in the presence of aluminium chloride in carbon disulfide at 60-70° for 8 h [141,619] according to [139]. SM was obtained by reaction of p-nitrobenzoyl chloride with p-methylphenetole in the presence of aluminium chloride. 

Also obtained (by-product) by diazotization of 2-amino-5-nitrobenzophenone (4%). The 2-nitrofluorenone was the major compound obtained (75%) [539]. Also obtained (poor yield) by Fries rearrangement of p-nih Ophenyl benzoate with aluminium chloride in nitrobenzene at 170° for 1 h (4%) [540]. Preparation from 2-nitrothioxanthen-9-one 10,10-dioxide (SM) by a three-step synthesis SM by refluxing in a solution of 2% sodium hydroxide in dioxane/ water mixture (65 35) for 2 h, gave the 2-(2-hydroxy-5-nitrobenzoyl)phenyl-sulfmic acid (89%). The former by reaction with mercuric chloride in refluxing aqueous acetic acid for 4 h led to the 2-chloromercuri-2 -hydroxy-5 -nitro-benzophenone (82%). Removal of the chloromercury group was achieved with concentrated hydrochloric acid in refluxing ethanol for 2 h (84%) [62]. 

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