Bromobenzene, condensation with

Bromoacetyl fluoride, 45, 6 Bromobenzene, condensation with 1 -phenyl- 2,2,2 - trichloroethanol, 48, 28... 

Aromatic compounds without substituents promoting electrophilic substitution or with substituents poor in this respect can be forced to condense with tellurium tetrachloride at higher temperatures in the presence of aluminum trichloride4,5 (Table 16, p. 529). In this manner, benzene, toluene, chlorobenzene, and bromobenzene were converted to diaryl tellurium dichlorides. 

Halogenated aromatic compounds can be condensed with alkyl or aryl halides by using copper to remove the halogen Zincke350 prepared ethyl phenylacetate in this way from bromobenzene and ethyl chloroacetate and Ullmann and his co-workers351 prepared biaryls from 2 moles of aryl halide and copper (for a review see Fanta352). 

Tetralones, tndanones. In the presence of this complex base a,/3-unsaturated ketones condense with bromobenzene to form tetralones and/or indanones. Benzyne is the actual reactant. ... 

The synthesis of SFs-substituted phenothiazine was disclosed in a patent from Smith, Kline French Laboratories (63USP3107242). 3-SFs-Acetanilide (120), prepared by acetylation of d-SFs-aniline (39) with acetic anhydride, was first condensed with bromobenzene under basic conditions, in the presence of Cul and copper-bronze powder, and after add hydrolysis provided 3-SFs-diphenylamine (121). This product was then fused with sulfur in the presence of a catalytic amount of iodine to give 2-SFs-phenothiazine (122) in unreported yield (Scheme 34). 

The aromatic semiflexible polyesters can be formed by varying the dicarboxylic multi phenyl acid structure (naphthalene and diphenol) and non-linear aromatic diol (3,4 -dihydroxybenzophenone). 3,4 -dihydroxybenzophenone can be synthesized from 4-methoxy bromobenzene and m-methoxybenzonitrile via multistep reaction, which can be condensed with respective diacid chloride in o-dichlorobenzene at reflux temperature [43]. It is well known that dimethyl siloxane spacer can make a flexible/semiflexible LC polymer. Thermotropic flexible liquid-crystalline main chain polyesters... 

Two benzyl entities having opposite polarity condense with particular ease. It suffices to add half an equivalent of phenyllithium to bromobenzene to obtain bibenzyl (1,2-diphenylethane) quantitatively. " Applying this method to l,3-di(bromomethyl)-benzene opens a facile entry to the strained [2.2]metacyclophane (118 Scheme 1-84). ... 

Ullman reaction The synthesis of diaryls by the condensation of aromatic halides with themselves or other aromatic halides, with the concomitant removal of halogens by a metal, e.g. copper powder thus bromobenzene gives diphenyl. The reaction may be extended to the preparation of diaryl ethers and diaryl thio-ethers by coupling a metal phenolate with an aryl halide. 

Fit a 50 ml. round-bottomed flask to a reflux water-condenser fitted with a calcium chloride tube. Dissolve 1-05 ml. of dry bromobenzene in 5 ml. of dry ether and add this solution to 0-25 g. of magnesium contained in the round-bottomed flask. Now add a crystal of iodine so that it rests on the magnesium. Warm if necessary to start the reaction if the latter becomes too vigorous immerse the flask in cold... 

Method 1. Arrange the flask containing the reaction mixture for steam distillation as in Fig. II, 40, 1. Proceed with the steam distillation until crystals of p-dibromobenzene appear in the condenser. Change the receiver and continue with the distillation until all the p-dibromobenzeiie has passed over from time to time run out the water from the condenser so that the crystals melt and run down into the receiver. Reject the residue in the flask. Transfer the first distillate to a separatory funnel, wash it with a httle water, and dry the lower layer with a little anhydrous magnesium sulphate or anhydrous calcium chloride filter. Distil slowly from a small distilling flask use a wire gauze or an air bath (Fig. II, 5, 3). Collect the fraction which passes over at 150-170° pour the residue (R), while it is still hot, into a small beaker or porcelain basin for the isolation of p-dibromobenzene. Redistil the fraction of b.p. 150-170° and collect the bromobenzene at 154-157° (3). The yield is 60 g. 

In a 2-1. three-necked flask, fitted with a separatory funnel, reflux condenser and stirrer, is placed 27 g. (-i.i moles) of magnesium turnings. A mixture of 30 g. of bromobenzene and 70 cc. of dry ether is run in and the flask warmed gently with a free flame until the reaction becomes rapid. Stirring is then started and the vessel is surrounded by a dish of cold water. A mixture of 151 g. of bromobenzene (total 181 g., 1.15 moles) and 380 cc. of dry ether is run in at such a rate as to cause vigorous refluxing when the addition is complete (one hour) the whole is stirred for ten minutes. 

To the dry salt is added 0.3 g. of copper powder (Note 2), 81 g. (0.51 mole) of bromobenzene, and a few drops of guaiacol (Note 3). The mixture is stirred thoroughly with a glass rod the flask is fitted with an air condenser and heated in a metal bath (Note 4). A reaction becomes evident at a bath temperature of 160-180°, liquefaction occurs, and the color of the mixture changes to red or purple. The temperature is gradually raised to 200° and maintained at 200° for 2 hours. 

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