Anisole p-bromo

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... 

Tri-p-anisylarsine, (CH30.C8Hg)3As, obtained from p-bromo-anisole, using the Fittig reaction, crystallises from alcohol-benzene in colourless, transparent, cubical crystals, M.pt. 156° C. 

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)... 

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. 

The carbanion of cyclohexyhdeneacetonitrile reacts with p-bromo and p-iodo-anisoles and 1-iodonaphthalene to afford good yields of the isomeric substitution products (60 to 69%) at Cy together with traces of 2,2-(diaryl)cyclohexyhdene acetonitrile ... 

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 ... 

As shown in Scheme 3, 4-bromo-2,6-bis(hydroxymethyl)anisole (16) [11], derived from p-bromophenol (14) by treatment with 37% aq. formaldehyde at room temperature for 12 days, followed by methylation with dimethyl sulfate and... 

Alkoxynaphthalenes are converted to 1-chloro- or l-bromo-2-alkoxynaphtha-lenes in near quantitative yield using copper(II) chloride or bromide. 1-Alkoxy-naphthalene affords about 70% l-alkoxy-4-bromonaphthalene with copper(II) bromide. Similarly, anisole gives a mixture of o- and p-haloanisoles. The absence of meta isomer is believed to provide evidence for the intermediacy of a radical cation of anisole.127)... 

Friedel-Crafts alkylations of chlorobenzene, chloropropylbenzenes, and p-xylene by cyclopropane have been examined, employing sulphuric acid and aluminium trichloride as catalysts. The alkylation of benzene, toluene, and anisole by 1-bromo-1-fluorocyclopropane results in indanes, indenes, and alkenylbenzenes. Intramolecular acylation of (183) affords products of attack at C-1 and C-2 of the cyclo-... 

For the catalytic asymmetric FC reaction, the application of chiral titanium complexes of BINOL derivatives was first realized by Mikami and coworkers in the reaction of electron-rich aryl and vinyl ethers with fluoral [245]. For the FC reaction of anisole, it was found that the catalytic activity and enantioselectivity of BINOL-Ti catalysts were critically influenced by the substituents of BINOL derivatives. The electron-withdrawing bromo atoms at 6,6 -positions of BINOL turned out to be beneficial to the catalysis, the trifluoroethanol derivatives were obtained in high yield (89%) and up to 90% ee with a p o isomer ratio of 4 1. The FC reaction of vinyl ether with fluoral catalyzed by BINOL-TiCb (10 mol%) gave a mixture of allylic alcohols in which the major isomer was usually the Z-alkene. The increase of bulkiness of silyl group is favorable for the formation of FC products with very high enantiomeric excess (Scheme 14.105). 

Preparation by demethylation of 4-bromo-4 -methoxybenzophenone (SM) with aluminium chloride in refluxing benzene for 8 h. SM was obtained by Friedel-Crafts acylation of anisole with p-bromobenzoyl chloride [917],... 

Bromoboration Reactions. BBrj does not add to isolated double bonds, but reacts with allene spontaneously even at low temperature to give (2-bromoallyl)dibromoborane, which provides stable (2-bromoallyl)diphenoxyborane by the addition of anisole. The diphenoxyborane derivative reacts with carbonyl compounds to give 2-bromohomoallylic alcohols in high yields (eq 12). Bromoboration of 1-alkynes provides (Z)-(2-bromo-l-alkenyl)dibromoboranes stereo- and re-gioselectively (eq 13), which are applied for the synthesis of trisubstituted alkenes, a,p-unsaturated esters, and 7,8-unsaturated ketones, bromodienes, 1,2-dihalo-l-alkenes, 2-bromoalkanals, and (3-bromo-oi,3-unsaturated amides. ... 

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