4-Bromobenzoyl bromide

The bromobenzoyl (bromide of benzoyl) is a large foliated, crystalline mass of a brownish color, soft and at common temperature nearly semifluid. It melts by a gentle warmth into a brownish yellow fluid. It possesses an analogous odor to the chloride, though much fainter and therefore aromatic. In the air it smokes faintly, but fumes strongly upon a slight elevation of temperature. It is combustible and bums with a bright and smoky flame. 

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). 

The four related compounds oxalomycin (157), neooxalomycin (158), cur-romycin A (159), and curromycin B (160) were reported in 1985 157 and 158 were isolated from a yet to be identified Streptomyces species (79, 80) and 159 and 160 from an ethidium bromide-treated strain of S. hygroscopicus (81, 82). The absolute configuration of oxalomycin (157) and neooxalomycin (158) has been determined by application of a combination of X-ray crystallography and chemical correlation to degradation products, the important derivatives being the p-bromobenzoate 161, obtained from 157 by ozonolysis-reduction, acetylation, partial hydrolysis, and reacylation with p-bromobenzoyl chloride, and the erythro acetate 162 which was obtained along with the threo compound 163 after acetylation of the ozonolysis products of 157 (79, 80). No stereochemical infor-... 

METHYL SULFOXIDE (67-68-5) CjHjOS (CHjIjSO Combustible liquid [explosion limits in air (vol %) 2.6 to 63.0 flashpoint 203°F/95°C oc autoignition temp 419°F/215°C Fire Rating 2]. Violent or explosive reaction with strong oxidizers, acryl halides, aryl halides and related compounds, alkali metals p-bromobenzoyl acetanilide, boron compounds, especially hydrides iodine pentafluoride, magnesium perchlorate, methyl bromide, perchloric acid, periodic acid, silver fluoride, sodium... 

Unlike aryl chlorides, acyl chlorides are quite reactive, although not often used. Oxidative addition of palladium(O) to the acid chloride 5.44 generates an acyl palladium(II) complex 5.46 (Scheme 5.12). This may undergo decarbonylation or not prior to alkene insertion depending on the reaction conditions, and the substrate structure (Schemes 5.13 and 5.14). Acid chlorides are more reactive than aryl bromides and selective coupling at the two positions of p-bromobenzoyl chloride 5.53 with different alkenes is possible (Scheme 5.15). ... 

Obtained by reaction of 3-bromobenzoyl chloride with 3-methoxyphenylmagnesium bromide [1620], (98%) [1621]. 

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