4-bromobenzoyl chloride

Another interesting example encountering numerous applications was reported by Bolton et al It comprises the implementation of a commercially available high-loading nucleophilic resin 9 for the removal of excess starting material 2-bromobenzoyl chloride (28) during the synthesis of a simple amide such as that of A-benzyl-2-bromo-A-methylbenzamide (29), as indicated in Fig. 11. 

N-Benzyl-2-bromo-N-methyl-benzamide (35). A suspension of morpholine resin (3, 0.63 mmol) in DCM (2 ml) was treated with. V-methyl-benzylamine (0.23 mmol) and 2-bromobenzoyl chloride (0.146 mmol). The reaction mixture was shaken for 5 h. Isocyanate resin (15, 0.2 g) was added followed by DCM (1 ml). The reaction mixture was then shaken for 16 h. Filtration of the resin followed by concentration of the filtrate gave the purified product. 

Pyridones may be selectively acylated at oxygen by treatment with acetyl chloride in acetone in the presence of potassium carbonate <2001JOC3646>. 2-Pyridones are also selectively O-acylated with 2-bromobenzoyl chlorides in high yield using potassium carbonate and tetrabutylammonium bromide (TBAB) in acetone <2003T3009>. For example 3-methoxy-2(17/)-pyridone is acylated in 88% yield by 2-bromobenzoyl chloride under these conditions (Equation 73). 

Preparation by reaction of 2-bromobenzoyl chloride with 4-methoxytoluene in the presence of aluminium chloride. 

Preparation by reaction of 2-bromobenzoyl chloride with 4-chloroanisole in the presence of aluminium chloride in refluxing methylene chloride overnight (96%) [1682],... 

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