1- Bromo-2-phenylpropane

Micellar microenvironments may be used for differentiating courses of reaction. Thus, cationic micelles efficiently suppressed the SN1 reaction of 1-bromo-2-phenylpropane (Lapinte and Viout, 1973) and of 3-bromo-3-phenylpropionate (Bunton et al., 1974). Tagaki et al. (1976) found that the facilitated formation of carbanion intermediates changed the course of reaction of p-nitrophenyl esters. 

Competitive SN1, SN2, and E2 reactions of 1-bromo-2-phenylpropane 195) have also been investigated in the absence and presence of cationic surfactants 190 ... 

Bromoadamantane and 1-bromoadamantane are reduced to adamantane in yields of 84% and 79%, respectively, when treated with triethylsilane and catalytic amounts of aluminum chloride.186 Similar treatment of benzhydryl chloride and exo-2-bromonorbomane gives the related hydrocarbons in yields of 100% and 96%, respectively.186 In contrast, 2-bromo-l-phenylpropane gives only a 43% yield of 1-phenylpropane the remainder consists of Friedel-Crafts alkylation products.186 Some alkyl halides resist reduction by this method, even when forcing conditions are employed. These include p-nitrobenzyl bromide, 3-bromopropanenitrile, and 5-bromopentanenitrile.186... 

BtURET, 1-PHENYL-2-THIO-, 42,87 Bromination, of 2-aminopyridine, 44,34 of l-bromo-3-phenylpropane with N-bromosuccinimide to give 1,3-dibromo-l-phenylpropane,... 

The l-bromo-3-phenylpropane was obtained from Columbia Organic Chemicals Co., Inc., Columbia, South Carolina, and from Aldrich Chemical Co., Inc., Milwaukee, Wisconsin. Redistillation of the commercial material does not noticeably affect yields. 

Bromo-3-phenylpropane Benzene, (3-bromopropyl)- (8,9) (637-59-2) Triphenylphosphine Phosphine, triphenyl- (8,9) (603-35-0)... 

Phenylpropyltriphenylphosphonium bromide (1) was prepared using the following procedure A solution of 1 equiv of 1-bromo-3-phenylpropane and 1.05 equiv of triphenylphosphine (both obtained from Aldrich Chemical Company, Inc.) in dry toluene is heated at reflux for 50 hr. The resulting solids are collected by vacuum filtration, washed on the filter three times with dry pentane, and dried at 100°C/1 mm for 6 hr affording 1 in 87-92%yield. 

The structural elements can be assembled in only one way and this identifies the compound as 1-bromo-3 -phenylpropane. 

Chiral (5)-2-(methoxymethyl)-l -[( )-3-phenyl-2-propenyl]pyrrolidine obtained from (S)-2-(meth-oxymethyl)pyrrolidine26,30 and ( )-3-bromo-1-phenyl-1-propene, is deprotonated by potassium rert-butoxide/ferf-butyllithium27-28 generating the chiral allyl carbanion, the alkylation of which affords the enamines, which can be hydrolyzed to give 3-alkylated 3-phenylpropanals. 

The symmetry of this hydrocarbon makes possible a self-coupling reaction with 2-bromo-2-phenylpropane. 

Dehydrobromination of 2,3-dibromo-l,l,l-trifluoro-3-phenylpropane (30) and 2-bromo-3,3,3-trifluoro-l-phenylprop-l-ene (31) leads to 3,3,3-trifluoro-1-phenylprop-1-yne (32).62... 

A-7. Provide two methods for the synthesis of 1-bromo-l-phenylpropane from an aromatic hydrocarbon. 

A novel ionic liquid methodology for pyrrole C-alkylation is described (Equation 136) <20050L1231>. The pyrrole alkylation is achieved with various simple alkyl halides (1-bromopentadecane, l-(bromomethyl)-, l-(3-chloropropyl)- and l-(3-iodopropyl)benzenes, 2-(2-bromoethyl)- and 2-(3-bromopropyl)naphthalenes) and mesylates (3-phenylpropyl-, l-methyl-3-phenylpropyl-, 2-(2-naphthyl)ethyl- and 3-(2-naphthyl)propyl methanesulfonates) selectively at C(2)- and C(5)-positions in good yields with minimal by-products under relatively mild conditions in various ionic liquids. 2-(3-Phenylpropyl)pyrrole 569 was synthesized from pyrrole and l-bromo-3-phenylpropane in a mixed solvent system, [Bmim][SbF6] and MeCN, in 81% yield at 115°C for 44h with 5% yield of dialkylated compound. 

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