Sulfinyl bromide bromination

Opening an unused but old commercial ampoule of the ice-cooled bromide led to eruption of the decomposed contents [1]. Similar occurrences on 2 occasions were reported later [2], though on both occasions hexabromonaphthalene was identified in the residue (suggesting contamination of the bromide by naphthalene as an additional source of internal pressure). Sulfinyl bromide is of limited stability, decomposing to sulfur, sulfur dioxide and bromine, and so should be stored under refrigeration and used as soon as possible. 

The sulfinyl bromide (80) was also prepared using A(-bromosuccinimide as the oxidizing agent (Ishimaru and Imamoto, 1975). Further oxidation of 80 with iV-bromosuccinimide in the presence of benzoyl peroxide followed by treatment of the product (81) with triethylamine gave the 3-bromomethylcephem (82) in 33% yield. Displacement of the bromine using silver acetate in acetic acid resulted in the cephem (83) in 45% yield. 

ETHANOL (64-17-5) CjHjOH Flammable liquid. Forms explosive mixture with air [explosion limits in air (% by volume) 3.3 to 19 flash point 55°F/13°C 68°F/20°C (80%) 72°F/22°C (60%) 79°F/26°C autoignition temp 685°F/363°C Fire Rating 3], Reacts, possibly violently, with strong oxidizers, strong acids bases, strong peroxides acetic anhydride, acetyl bromide, acetyl chloride, aliphatic amines, bromine pentafluoride, calcium oxide (quicklime), cesium oxide, chloryl perchlorate, disulfiiryl difluoride, ethylene glycol methyl ether, iodine heptafluoride, isocyanates, nitrosyl perchlorate, perchlorates, platinum, platinum-black catalyst potassium-tert-butoxide, potassium, potassium oxide, potassium peroxide, potassium superoxide phosphorus (III) oxide, silver nitrate, silver oxide, sulfuric acid, oleum, sodium, sodium hydrazide, sodium peroxide, sulfinyl cyanamide, tetrachlorosilane, s-triazine-... 

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