5-methoxyphenyl bromide

The 6-endo-tng Mizoroki-Heck cyclization was also used in a few syntheses of more complex systems, especially for the formation of phenylcarbazols of type 176, which are potential anticancer agents (Scheme 5.32). In the cyclization of aryl bromide 175, a new aromatic ring is formed which might allow for high yields (175 176) [73]. In addition, 2-naphthyl triflates [74], as well as naphthyl bromides, 5-methoxyphenyl bromide and... 

Diacetoxy acetophenone 1 -p-Methoxyphenyl-2-benzylamino propane Hydrogen bromide... 

Bromo-4 -benzyloxypropiophenone 2-(4-Methoxyphenyl)ethylamine Hydrogen bromide... 

Polyphosphoric acid is a commonly used catalyst for this reaction however, in some cases a mixture of hydrogen bromide/acetic acid gives better results. Acylation of the S-phenyl-, V-(4-tolyl)- or S-(l-naphthyl)-substituted thiobenzenepyruvic acids 3a-c affords the corresponding dibenzo[A,/]thiepins in satisfactory yields, while reaction of the S-(4-methoxyphenyl) or S-(2-naphthyl) derivatives fails to provide any thiepin.60 The intramolecular Friedel-Crafts acylation of 2-(arylsulfanyl)benzeneacetic acids also yields the corrresponding dibenzothiepins in this case the use of hydrogen fluoride sometimes results in purer products.38 The applicability of this method is restricted to the synthesis of stable bisannulated thiepins. 

Whereas the nucleophilic addition of vinylmagnesium bromide to a-alkoxy aldehydes (12, 16) proceeds with a low to moderate chelation-controlled diastereoselectivity, a remarkably high preference for the opposite stereochemical behavior is found with the jS-silyl phosphorus ylide 1477. Due to the electron-donating 4-methoxyphenyl substituents at the phosphorus atom, as well as the /i-methyldiphenylsilyl group, 14 is an excellent vinylation reagent which does not lead to any Wittig olefination products. 

Methoxyphenyl)-2-phenyl-lH-imidazole. A 2-L, three-necked, round-bottomed flask equipped with an addition funnel, reflux condenser, and mechanical stirrer is charged with 500 mL of tetrahydrofuran (THF) and 125 mL of water. Benzamidine hydrochloride monohydrate (50 g, 0.29 mol) (Note 1) is added, followed by the slow, portionwise addition of potassium bicarbonate (54.4 g, 0.57 mol) (Note 2). The reaction mixture is vigorously heated to reflux. A solution of 4-methoxyphenacyl bromide (65.3 g, 0.29 mol) in 325 mL of THF is then added dropwise via the addition funnel over a period of 30 min while the reaction is maintained at reflux. After completion of the addition, the mixture is heated at reflux for 18-20 hr (Note 3), then cooled in an ice bath (Note 4), and THF is removed under reduced pressure using a rotary evaporator. An additional 100 mL of water is added, and the resulting suspension is stirred at 50-60°C for 30 min. The mixture is cooled in an ice bath and the solids are collected by filtration. The filter cake is rinsed with two 100-mL portions of water and air-dried in the filter funnel for 2 hr. The crude product is transferred to a 500-mL flask and 150 mL of diisopropyl ether and 150 mL of hexanes are added. The mixture is stirred for 2 hr at room temperature, and the solids are again collected by filtration. The filter cake is dried in a vacuum oven for 48 hr (68°C/ca. 100 mm) to give 68.6 g (96%) of the desired imidazole as an off-white solid (Notes 5, 6). 

Bis(p-methoxyphenyl) ditelluride (typicalprocedure To a solution of p-methoxyphenyl-magnesium bromide (prepared from p-bromoanisole (5.82 g, 0.0311 mol) and Mg (1.0 g, 0.042 mol) in THF (20 mL)) is added Te shot (3.81 g, 0.0300 mol) at room temperature. The mixture is stirred under reflux for 3 h and then cooled to 0°C and treated with a sam-rated solution of NH Cl (20 mL vigorous evolution of gas). The mixture is filtered through Celite and the solids washed with saturated solution of NH Cl and ether. The organic phase is washed with brine and dried with Na2S04. Evaporation of the solvent and recrystaUiza-tion from CHClj/petroleum ether affords the pure product (5.16 g (75%) m.p. 57-59°C). 

Abstract. Grignard reactions are of utmost importance in organic synthesis (Lee, 2005), and finding the prime conditions under which to conduct these reactions is really crucial to their usefulness. This work looks at the effects of time, and temperature on yield in the reaction of isopropyl magnesium bromide with 4-methoxyben-zaldehyde to produce l-(4-methoxyphenyl)-2-methylpropan-l-ol. The reaction was first run for 10 min at 25, 50, 75, and 80 °C. Next it was run at 80 °C for 10, 20, and 30 min (see Methods section for more details). Highest yields (85%) were obtained at 80 °C with 10-20 min reaction times. Utilizing conditions that optimize yields will improve the economic practicality of these reactions, and increase their usefulness as a synthetic tool. 

It is synthesized by the reaction of 3,4-dimethoxyphenyl-2-amine and l-(4-methoxyphenyl)-3-butanone with a simultaneous reduction of formed imine, giving the product (11.1.30), the methoxyl-protecting groups of which are cleaved by hydrogen bromide, giving dobutamine (11.1.31) [32,33]. 

Hexestrol Hexestrol, 4,4 -(l,2-diethylethylene)diphenol (28.1.29), is a derivative of a,j3-diphenylethane, and it is a synthetic estrogen. Hexestrol is made in a Wurtz dimerization reaction of l-bromo-l-(4-methoxyphenyl)propane (28.1.27) in the presence of sodium, magnesium, aluminum, or iron. The initial l-bromo-l-(4-methoxyphenyl)propane (28.1.27) is made in turn by addition reaction of hydrogen bromide to 4-methoxy-l-propenylbenzene. Subsequent removal of the methoxy protective groups from the resulting dimerization product (28.1.28) using hydroiodic acid gives hexestrol (28.1.29) [37-43]. 

The elimination of C1F from a scries of compounds RCH(OH)CCl2CF3 using the system aluminum (1.2 equiv) and lead(II) bromide (O.lequiv) with R = phenyl, 4-methoxyphenyl, 1-mesylindol-3-yl, cyclohexyl or zinc/aluminum(III) chloride with R = CHMePh, phenyl, 3,4-di-chlorophenyl, 1-phenylethyl, cyclohexyl has been described.180181... 

The N-arylation reactions are investigated more seldom than the N-alkylation ones. N-Arylation of 5-phenylte-trazole with bis-(4-methoxyphenyl)iodonium bromide in MeOH in the presence of Et3N yielded only the N2-isomer 260 (Equation 42) <2001CHE372>. 

To a slurry of 11.7 g (0.33 mole) of methyltriphenylphosphonium bromide in 150 ml of dry tetrahydrofuran at -35°C was added, over a 15-minute period, 20 ml (0.033 mole) of n-butyl lithium. The reaction mixture was stirred for one hour. To the reaction mixture at -35° to -40°C was added over a 10-minute period a solution of 5.7 g (0.0165 mole) of 3-chloro-5,6-bis(4-methoxyphenyl)-l,2,4-triazine in 50 ml of tetrahydrofuran. The reaction mixture was allowed to warm to ambient temperature and was stirred overnight. A solution of 1.05 g (0.0165 mole) of sodium carbonate in 50 ml of water was added dropwise to the reaction mixture which then was heated at reflux for three hours. The reaction mixture was cooled, poured over ice, and extracted with diethyl ether. The diethyl ether extract was washed with water, dried over anhydrous sodium sulfate, and concentrated. The concentrate was chromatographed over silica gel, with three fractions being collected. After evaporation of solvent, the third fraction solidified MP about 109°-113°C. 

Amino-8-oxo-3-vinyl-5-thia-l-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid 4-methoxyphenyl ester 4-Bromoacetyl bromide Sodium nitrite Trifluoroacetic acid... 

By interaction of 7-amino-8-oxo-3-vinyl-5-thia-l-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid 4-methoxyphenyl ester with 4-bromoacetyl bromide was prepared 7-(4-bromo-3-oxo-butyrylamino)-8-oxo-3-vinyl-5-thia-l-azabicyclo (4.2.0)oct-2-ene-2-carboxylic acid 4-methoxyphenyl ester. The active methylene group in that product was then nitrosated with sodium nitrite. The initial product spontaneously tautomerizes to afford 7-(4-bromo-2-hydroxyimino-3-oxo-butyrylamino)-8-oxo-3-vinyl-5-thia-l-azabicyclo(4.2.0) oct-2-ene-2-carboxylic acid 4-methoxyphenyl ester. By the reaction of that compound with thiourea and then with trifluoroacetic acid was obtained (6R,7R)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-8-oxo-3-vinyl-5-thia-l-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid sodium nitrite, (Z)-oxime (Cefdinir sodium nitrile). 

Transmeta Nation of a fluoroalkynylzinc reagent to copper bromide and cross-coupling preparation of 1-(4-methoxyphenyl)-1-perfluorohexyne18... 

Electrochemical preparation of an arylzinc bromide and its coupling with 2-chloropyridine synthesis of 2-(4-methoxyphenyl)pyridine... 

Phenylethyl) trimethylammonium-2-14C bromide, (2-Phenylethyl) trimethylammoni-um-l-14C bromide, [2-(p-methoxyphenyl)ethylltrimethylammonium-2-14C bromide, [2-(p-methoxyphenyl) ethyl] trimethylammonium-1-C bromide, [2-(p-chlorophenyl) ethyl]-... 

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