F 2-Bromopropane

Bromoform, 0368 f Bromomethane, 0429 f l-Bromo-3-methylbutane, 1984 f l-Bromo-2-methyIpropane, 1633 f 2-Bromo-2-methyIpropane, 1634 f 2-Bromopentane, 1985 f 1-Bromopropane, 1241 f 2-Bromopropane, 1242... 

Prop-2-enyl trifluoromethanesulfonate, 1457 Propionyl hypobromite, 1150 Propionyl nitrite, 1181 Propiophenone, 3145 f Propyl acetate, 1971 f Propyl bromide, see 1-Bromopropane, 1237 f Propyl chloride, see 1-Chloropropane, 1239 Propylcopper(I), 1247... 

BROMOPROPANE (106-94-5) Forms explosive mixture with air (flash point 78°F/26°C). Strong oxidizers may cause tire and explosions. 

If you want to synthesize an alkene, you should choose the most hindered alkyl halide possible in order to maximize the elimination product and minimize the substitution product. For example, 2-bromopropane would be a better starting material than 1-bromopropane for the synthesis of propene because the secondary alkyl halide would give a higher yield of the desired elimination product and a lower yield of the competing substitution product. The percentage of alkene could be further increased by using a sterically hindered base such as f rf-butoxide ion or DBN instead of hydroxide ion (Section 10.10). 

AMINO GROUP Boron trifluoride ether-ate. 1-/-B utyloxy carbony ltriazole-1,2,4. Di-f-butyl dicarbonate. 4-Dimethylamino-1-f-butyloxycarbonyl pyridinium chloride. CARBONYL GROUP Ceric ammonium nitrate. 1,2-Dihydroxy-3-bromopropane. Sodium N-chloro-p-toluenesulfonamide. Thallium(III) nitrate. Trichloroethanol. Trimethylsilyl cyanide. Chloromethyl methyl sulfide. N,N -Diisopropylhydra-zine. Trichloroethanol. 

As for the introduction of a secondary alkyl moiety to the 1-hydroxy oxygen, the usual alkyl halide method has given poor results. However, employing preformed cesium salt of 1-hydroxyindoles in DMF, this difficulty has been overcome (Scheme 9) [24]. Thus, the reaction of Nb-methoxycarbonyl-1-hydroxytryptamine (52) with methyl 2-bromopropionate, 2-bromopropane, cyclohexyl bromide, and 1-phenethylbromide gives birth to the corresponding l-(l-methoxycarbonyl)ethoxy (53a, 88%), l-(2-propyl)oxy (53b, 87%), 1-cyclohexyloxy (53c, 19%), and l-(l-methyl)benzyloxy derivatives (53d, 80%), respectively. l-t-Butyldimethylsilyloxy-M)-methoxycarbonyl-tryptamine (54) can be obtained by the conventional f-butyldimethylsilyl chloride and imidazole method [24]. 

BF3-etherate added to 2-bromopropanal dimethyl acetal at ca. 5°, and ketene (generated by the pyrolysis of acetic anhydride) bubbled into the mixture for 30 min intermediate ester (Y 85%), added dropwise to a stirred dispersion of KOH in DMF at 0°, stirring continued for 2 h, treated with further powdered KOH at 1 hourly intervals (for a further 4 h), and acidified with 1 M HCl product (Y 84%). F.e.s. P.B. Rasmussen, S. Bowadt, Synthesis 1989, 114-7. 

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