3- Bromo-l-propanol

In 1618 Abderhalden and Eichwald0 made the curious observation that dextrorotatory propylene oxide yields levorotatory l-bromo-2-propanol on treatment with hydrogen bromide- Subsequent work by Levene and Walti1016 confirmed this particular finding, but at the Bairn time called attention to certain defects in the previous study. There... 

Bis(2-hydroxypropyl ether) of Bisphenol-A (II). A mixture of the sodium salt of pure bisphenol-A (0.25 moles), l-bromo-2-propanol (1 mole) and tetrabutylammonium bromide (0.019 moles) ( ) in 600 mL of water containing NaOH (1.5 moles) was vigorously agitated at 50 C for 96 h under N2 blanket. 500 mL of methylene chloride was then added and agitated for 24 h. The organic layer was separated. The remaining work-up was similar to that used in the synthesis of compound I. 

Bromopropanoi caci d(t) 3-Bromopropanoi caci d 3-Bromo-1-propanol l-Bromo-2-propanol 2-Bromopropanoyl bromi de 2-Bromopropanoyl chi ori de c/si-Bromopropene fransl-Bromopropene 2-Bromopropene 3-Bromopropene... 

Dibromopropane from 2-bromopropane l-Bromo-2-propanol from 2-propanol l-Bromo-2-methyl-2-propanol from fert-butyl bromide... 

Reaction of propene with aqueous bromine gives the expected product l-bromo-2-propanol, but reaction of 3-bromo-l-propene with aqueous bromine gives 2,3-dibromo-l-propanol. Suggest a reason for this difference in regioselectivity. 

Hydrogen hahdes normally add to form 1,2-dihaLides, though an abnormal addition of hydrogen bromide is known, leading to 3-bromo-l-chloropropane [109-70-6], the reaction is beUeved to proceed by a free-radical mechanism. Water can be added by treatment with sulfuric acid at ambient or lower temperatures, followed by dilution with water. The product is l-chloro-2-propanol [127-00-4]. 

As a second exanple, consider the preparation of l-bromo-2-methyl-2-propanol from rcrr-butyl alcohol. 

HO—Br, then we can predict that addition of HOBr to 2-methylpropene will give l-bromo-2-methyl-2-propanol ... 

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