Bromo anisole

Zenitz obtained the analogous compounds 237 and 238 by the action of the corresponding a-cyano-w-bromo-w-alkanes on 2-methylindolyl magnesium bromide in ether. Eiter and Svierak prepared a-(3-indolyl)propionitrile (239) by the action of a-bromopropionitrile on indole magnesium iodide in anisole. ... 

Amyl bromide [Pentane, 1-bromo-], 82 Aniline [Benzenamine], 122 Anilines, o-alkylation of, 15 Anisole [Benzene, methoxy-], 48 Amsyl chloride [Benzene, l-(chloromethyl)-... 

At stage 1 of the synthesis, m-bromoanisole [1] and n-butyUithium are converted via bromo/lithium exchange in order to obtain m-lithium anisole [2] and n-bromobutane. At stage 11, the reaction mixture is treated with dimethylformamide, and then the reaction is quenched using 3 M hydrochloric acid. Tetrahydrofurane is used as solvent at both synthetic stages. 

A New Improved Synthesis of Tricycle Thienobenzazepines Apphcation of chemistry recently developed by Knochel" combined with the well-described halogen dance (HD) reaction, allowed preparation of our key intermediate A in only three synthetic transformations (Scheme 6.4). In this respect, treatment of 2-bromo-5-methylthiophene with hthium diisopropylamide followed by dimethylformamide afforded aldehyde 11 in good yield, lodo-magnesium exchange with conunercial 4-iodo-3-nitro anisole followed by reaction with 11 afforded the thiophene catbinol 12. Dehydroxylation of 12 provided our key intermediate A which presented the requisite functionality to examine our approach to the construction of the seven-member ring system. 

The checkers have prepared the following bromides by the same procedure w-chlorobromobenzene (b.p. 191-194°) from jw-chloroaniline in 91-94% yields ra-dibromobenzene (b.p. 215-217°) from ra-bromoaniline in 80 87% yields and u-bromo-anisole (b.p. 114-116°/29 mm.) from o-anisidine in 88-93% yields. In the preparation of o-bromoanisole the washing with sulfuric acid was omitted. 

Bromoanisole Anisole, p-bromo- (8) Benzene, 1-bromo-4-methoxy- (9) (104-92-7) Methyl iodide Methane, iodo- (8,9) (74-88-4)... 

More recently, 4-methylbenzyl 25 and 4-methoxybenzyl (Mob) protection17 was proposed for the selenol group. The 4-methylbenzyl group is introduced by reacting selenocysteine with a-bromo-p-xylene following essentially the procedure for the preparation of the related cysteine derivative. 25 This type of protection is applied in combination with the Boc/Bzl strategy and its removal is achieved by HF treatment in the presence of 15% anisole and 2.5% ethyl methyl sulfide at 0°C in one hour. Unfortunately, experimental details were not reported by Oikawa et al. 25 ... 

The fluorination of other activated aromatic compounds, such as anisole and phenol, undergo monofluorination mainly in the ortho and para positions, whereas the fluorination of deactivated aromatics, such as nitrobenzene, trifluoromethylbenzene and benzoic acid, give predominantly the corresponding meta fluoro-derivatives which is consistent with a typical electrophilic substitution process. Also, fluoro-, chloro- and bromo-benzenes are deactivated with respect to benzene itself but are fluorinated preferentially in the ortho and para positions [139]. At higher temperatures, polychlorobenzenes undergo substitution and addition of fluorine to give chlorofluorocyclohexanes [136]. 

Bromomethyl)anisole, AM90 l-Bromo-3-methylbutane, AE83... 

The reaction of p-iodo- or p-bromo-anisole or of 1-iodonaphthalene with the anion formed from the a,(3-unsaturated nitrile (36) gives 60-70% combined yields of the isomeric nitriles (37) and (38) together with small amounts of the diarylated derivatives (39).135... 

C4H7BrOj Ethyl bromo- 158.2 CtHsO Anisole 153.85 CioHn o-Pinene 155.8 <150.4 243... 

Laali et al.234 have developed a method to the highly selective pura-adamantylation of arenes (toluene, ethylbenzene, anisole) with haloadamantanes (1-chloro- and 1-bromoadamantane, l-bromo-3,5,7-trimethyladamantane) and 1-adamantanol promoted by triflic acid in butylmethylimidazolium triflate [BMIM][OTf] ionic liquid. In contrast to reactions mn in 1,2-dichloroethane, little or no adamantane byproduct was detected in [BMIM][OTf. Furthermore, no isomerization of para-tolyladamantane was observed supporting the intramolecular nature of the formation of meta isomers. In competitive experiments with benzene-toluene mixture (1 1 molar ratio), high substrate selectivities were found (kT/kB = 16-17) irrespective of the alkylating agent. This is in sharp contrast to values about unity measured in 1,2-dichloroethane. 

Alkoxy derivatives of biphenyl can be obtained either from alkoxy-anilines or by coupling with alkoxybenzenes. From diazotized p-bromo-aniline and anisole a 20% yield of 4-bromo-2 -methoxybiphenyl and a 7% yield of 4-bromo-4 -methoxybiphenyl are obtained. In connection with their studies on Cannabis Indica, Ghosh, Pascall, and Todd u prepared the highly substituted biphenyl compound, 2-cyano-5-methyl-2, 5 -dimethoxy-4 -n-amylbiphenyl (VII), in 27% yield from the nitrosoacetyl derivative of 2-cyano-5-methylaniline and 2,5-dimethoxy-n-amylben-zene. 

Carbanion 170 derived from cyclohexenylidene acetonitrile reacts with /7-bromo or p-iodo anisole to afford a mixure of 171a and 171b, the two isomers of the monosubstitution product (equation 110)203. 

Because of the different reactivities of iodo and bromo substituents in the Suzuki reaction, selective coupling can be realized. For example, 8-bromo-2-(4-methoxyphenyl)-l,10-phenanthroline (15) can be prepared by reacting the 4-boronic acid derivative of anisole with bromo(iodo)phenanthroline under Suzuki conditions (Eq. (44)) [75]. 

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