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To generate the mono-substituted product, a protection with acetyl chloride is required: Aniline can react with bromine even in room temperatures in water. Acetyl chloride is added to prevent tribromination. The reaction to form 4-bromoaniline is to protect the amine with acetyl chloride, then hydrolyse back to reform aniline.
Aniline reacts with acyl chlorides or carboxylic anhydrides to give anilides. For example, reaction of aniline with acetyl chloride provides acetanilide (CH 3 −CO−NH−C 6 H 5). At high temperatures, aniline and carboxylic acids react to give anilides. [1]
Acetyl chloride was first prepared in 1852 by French chemist Charles Gerhardt by treating potassium acetate with phosphoryl chloride. [4]Acetyl chloride is produced in the laboratory by the reaction of acetic acid with chlorodehydrating agents such as phosphorus trichloride (PCl 3), phosphorus pentachloride (PCl 5), sulfuryl chloride (SO 2 Cl 2), phosgene, or thionyl chloride (SOCl 2).
Benzylamine reacts with acetyl chloride under Schotten-Baumann conditions to form N-benzylacetamide. Schotten–Baumann reaction also refers to the conversion of acid chloride to esters. The reaction was first described in 1883 by German chemists Carl Schotten and Eugen Baumann. [1] [2]
4-Bromoaniline is a compound where an aniline molecule is substituted with a bromine atom on the para position. Commercially available, this compound may be used as a building block, e.g. in the preparation of monobrominated biphenyl via the Gomberg-Bachmann reaction .
Acetyl chloride. This reagent is also common in the laboratory, but its use cogenerates hydrogen chloride, which can be undesirable. [8] Ketene. At one time acetic anhydride was prepared by the reaction of ketene with acetic acid: [11] H 2 C=C=O + CH 3 CO 2 H → (CH 3 CO) 2 O =
Acetanilide can be produced by reacting acetic anhydride with aniline: [7]. C 6 H 5 NH 2 + (CH 3 CO) 2 O → C 6 H 5 NHCOCH 3 + CH 3 COOH. The preparation used to be a traditional experiment in introductory organic chemistry lab classes, [8] but it has now been widely replaced by the preparation of either paracetamol or aspirin, both of which teach the same practical techniques (especially ...
The Bogert–Cook synthesis (1933) involves the dehydration and isomerization of 1-β-phenylethylcyclohexanol to the octahydro derivative of phenanthrene [23] The Darzens–Nenitzescu synthesis of ketones (1910, 1936) involves the acylation of cyclohexene with acetyl chloride to methylcyclohexenylketone.