Chloro benzyl chloride

The p-chloro analog of phentermine has much the same activity as the parent compound, with perhaps a somewhat decreased activity on the central nervous system. Alkylation of p-chloro-benzyl chloride with the carbanion obtained from treatment of 2-nitropropane with strong base affords the compound containing the required carbon skeleton (74). Catalytic reduction of the nitro group yields chlorphentermine (75). ... 

N,N -Bis(2-Diethylaminoethyl)Oxamide Bis(2-Chlorobemochloride) A solution of 7 grams (0.025 mol) of N,N -bis(2-diethylaminoethyl)oxamide and 16.1 grams (0.1 mol) of 2-chloro-benzyl chloride in 100 ml of acetonitrile was refluxed for eleven hours. The solid which separated upon cooling was collected by filtration and recrystallized by dissolving it in... 

The ring-chiorinated benzyl chlorides are used ia the preparation of quaternary ammonium salts and as iatermediates for pharmaceuticals and pesticides. p-C. orohen zyl chloride is an iatermediate ia the manufacture of the rice herbicide, Saturn ((S-4-chlorobenzyl)-N,N-diethylthiolcarbamate [28249-77-6] (75). The o- and -chlorobenzal chlorides (l-chloro-2-and 4-dich1 oromethylhenzenes) are starting materials for the manufacture of o- and p- chlo rob enz aldehyde s. 

Benzyl chloride Toluene, a-chloro- (8) Benzene, (chloromethyl)- (9) (lQQ-44-7). 

Both methyltriethylphosphonium fluoride and methyltributylphospho-nium fluoride have been prepared The latter generates benzyl fluoride from benzyl chloride in 80% yield and ethyl fluoroacetate from ethyl bromoacetate in 53% yield Methyltnbutylphosphonium fluoride converts 1-bromododecane to a 50 50 mixture of 1-fluorododecane and 1-dodecene Methyltnbutylphosphonium fluoride also quantitatively forms styrene from 1-bromo-1-phenylethane [26] Methyl-tnbutylphosphonium fluonde is the reagent of choice for the conversion of N,N dimethylchloroacetamide to its fluoride, but it is not able to convert chloro-acetonitnle to fluoroacetomtrile Methyltnbutylphosphonium fluoride changes chloromethyl octyl ether to the crude fluoromethyl ether in 66% yield The stereoselectivity of methyltnbutylphosphonium fluoride is illustrated by the reac tions of the 2-tert-butyl-3-chlorooxiranes [27] (Table 2)... 

First, dimethylamino-2-phenoxyethane was made by reacting chloro-2-phenoxyethane with dimethylamine. Benzyl chloride (10 grams) was then added to a solution of 1-dimethylamino-2-phenoxyethane (12.3 grams) in acetone (35 ml). The mixture warmed spontaneously and N-benzyl-N,N-dimethyl-N-2-phenoxyethylammonium chloride slowly crystallized. After 24 hours, this solid was filtered off, washed with fresh acetone and dried immediately in vacuo, MP 135°-136°C. 

One route is described in U.S. Patent 2,986,573 Mix 63 grams of benzyl chloride, 38 grams of thiourea, 3 drops of concentrated ammonium hydroxide solution, and 250 ml of 95% ethanol. Reflux the mixture for 3 hours. Cool and add a solution containing 96 grams of 2,4-dichloro-nitrobenzene in 200 ml of ethanol. Heat the mixture to reflux and then add drop-wise a solution of 70 grams of potassium hydroxide in 500 ml of ethanol. Continue refluxing for 2 hours, and then cool and filter the solids produced. Wash the solid with aqueous ethanol and dry. There is thus produced 2-benzylthio-4-chloro-nitrobenzene. Sus-... 

C ( propyl) N phenylmtrone to N phenylmaleimide, 46, 96 semicarbazide hydrochloride to ami noacetone hydiochlonde, 46,1 tetraphenylcyclopentadienone to diphenyl acetylene, 46, 44 Alcohols, synthesis of equatorial, 47, 19 Aldehydes, aromatic, synthesis of, 47, 1 /3-chloro a,0 unsaturated, from ke tones and dimethylformamide-phosphorus oxy chloride, 46, 20 from alky 1 halides, 47, 97 from oxidation of alcohols with dimethyl sulfoxide, dicyclohexyl carbodumide, and pyndimum tnfluoroacetate, 47, 27 Alkylation, of 2 carbomethoxycyclo pentanone with benzyl chloride 45,7... 

As far as the reactions with benzyl chlorides are concerned (74), the oxidative addition of benzyl chloride and substituted benzyl chlorides to palladium atoms yields rj -benzylpalladium chloride dimers. The parent compound, bis(l,2,3-7 -benzyl)di-/i,-chloro-palladium(II), quantitatively adds four molecules of PEts by first forcing the rj -benzyl-iy -benzyl transformation, with subsequent breakage of the Pd-Cl bridges to form trans-bistPEtsKbenzyDchloroPddI). The spectral characteristics of the parent molecule are indicative of the allylic type of bonding. Similar i7 -benzyl compounds were formed from 4-methylbenzyl chloride, 2-chloro-l,l,l-trifluoro-2-phenylethane, and 3,4-dimethylbenzyl chloride. 

Secondary alcohols such as cyclohexanol or 2-butanol also react on heating for 20-120 min at 80 °C with TCS 14 in the presence of BiCl3 to give the chloro compounds cyclohexyl chloride 784 and 2-chlorobutane in 93 and 90% yield, respectively, HCl, and HMDSO 7 [11, 12]. Benzyl alcohol is transformed likewise by Me3SiCl 14 after 120 min. at 80 °C into benzyl chloride in quantitative yield. Analogously, esters such as 2-acetoxypropane 785 are also converted by TCS 14 in 100% yield into chloro compounds such as 786 and trimethylsilyl acetate 142. The yS-lactone 787 gives rise to 788... 

Sulphated zirconia catalysts can be acidic or superacidic depending on the method of treatment. A variety of acid-catalysed reactions, referred to earlier in this section, can be carried out with sulphated zirconia. Yadav and Nair (1999) have given a state-of-the art review on this subject. Examples of benzylation of benzene with benzyl chloride / benzyl alcohol, alkylation of o-xylene with. styrene, alkylation of diphenyl oxide with 1-dodecene, isomerization of epoxides to aldehydes, acylation of benzene / chlorobenzene with p-chloro benzoylchloride, etc. are covered in the review. 

Alkyl iodides, benzyl chlorides, benzyl bromides, and adamantyl bromides and iodides undergo reduction with triethylsilane/palladium chloride.195 The reduction of a /3-chloro ether occurs in excellent yield with this system (Eq. 56).195... 

CARBOBENZOXY CHLORIDE AND DERIVATIVES (Formic acid, chloro-, benzyl ester)... 

Lund and coworkers [131] pioneered the use of aromatic anion radicals as mediators in a study of the catalytic reduction of bromobenzene by the electrogenerated anion radical of chrysene. Other early investigations involved the catalytic reduction of 1-bromo- and 1-chlorobutane by the anion radicals of trans-stilhene and anthracene [132], of 1-chlorohexane and 6-chloro-l-hexene by the naphthalene anion radical [133], and of 1-chlorooctane by the phenanthrene anion radical [134]. Simonet and coworkers [135] pointed out that a catalytically formed alkyl radical can react with an aromatic anion radical to form an alkylated aromatic hydrocarbon. Additional, comparatively recent work has centered on electron transfer between aromatic anion radicals and l,2-dichloro-l,2-diphenylethane [136], on reductive coupling of tert-butyl bromide with azobenzene, quinoxaline, and anthracene [137], and on the reactions of aromatic anion radicals with substituted benzyl chlorides [138], with... 

The first clue to the existence of the SrnI mechanism came from product studies both in aliphatic and aromatic cases. It was noticed that in the reaction of benzyl and substituted benzyl chlorides with the 2-nitropropane anion, oxygen alkylation, yielding the oxime and then the aldehyde, occurs exclusively in the case of benzyl chloride and 3-nitrobenzyl chloride, whereas, with 4-nitrobenzyl chloride, the yield of aldehyde is only 6% and the carbon-alkylated (104) product is obtained in 92% yield (Kornblum, 1975). This was interpreted as the result of a competition between 8, 2 (O-alkylation) and S l (C-alkylation) reactions. In the aromatic case, it was observed that the reaction of 5- and 6-halopseudocumenes with KNHj in liquid ammonia (Kim and Bunnett, 1970) forms the 5- and 6-pseudocumi-dines in a ratio which is the same whether the starting compound is the 5- or 6-isomer in the case of the chloro- and bromo-derivatives, as expected from an aryne mechanism (Scheme 9), whereas much more non-rearranged... 

Chloro-3-hydrox34oluene, see p-Chloro-ro-cresol 2-Chloroisopropyl ether, see Bis(2-chloroisopropyl) ether p-Chloroisopropyl ether, see Bis(2-chloroisopropyl) ether Chloromethane, see Methyl chloride (Chloromethyl)benzene, see Benzyl chloride Chloromethyl bromide, see Bromochloromethane Chloromethyl ether, see sym-Dichloromethyl ether (Chloromethyl)ethylene oxide, see Epichlorohydrin (2-Chloro-l-methylethyl) ether, see Bis(2-chloroisoprop-yl)... 

Chloro-l-phenylethanone, see a-Chloroacetophenone 4-Chlorophenyl ether, see 4-Chlorophenyl phenyl ether p-Chlorophenyl ether, see 4-Chlorophenyl phenyl ether Chlorophenylmethane, see Benzyl chloride [(2-Chlorophenyl)methylene]propanedinitrile, see o-... 

Chloropropylene oxide, see Epichlorohydrin Y Chloropropylene oxide, see Epichlorohydrin 3-Chloro-l,2-propylene oxide, see Epichlorohydrin Chlorothane NU, see 1,1,1-Trichloroethane Chlorothene, see 1,1,1-Trichloroethane Chlorothene NU, see 1,1,1-Trichloroethane Chlorothene VG, see 1,1,1-Trichloroethane a-Chlorotolnene, see Benzyl chloride Q-Chlorotolnene, see Benzyl chloride... 

Benzyl chloride undergoes further chlorination to give di- and tri-chloro derivatives, though it is possible to control the extent of chlorination by restricting the amount of chlorine used. As indicated above, it is easier to mono-brominate than it is to mono-chlorinate. The particular stabilization conferred on the benzylic radical by resonance is underlined by the reaction of ethylbenzene with halogens. 

Benzylic halides are reduced very easily using complex hydrides. In a-chloroethylbenzene lithium aluminium deuteride replaced the benzylic chlorine by deuterium with inversion of configuration (optical purity 79%) [537]. Borane replaced chlorine and bromine in chloro- and bromodiphenylme-thane, chlorine in chlorotriphenylmethane and bromine in benzyl bromide by hydrogen in 90-96% yields. Benzyl chloride, however, was not reduced [5iSj. Benzylic chlorine and bromine in a jy/n-triazine derivative were hydrogeno-lyzed by sodium iodide in acetic acid in 55% and 89% yields, respectively [5i9]. 

Cross coupling between an aryl halide and an activated alkyl halide, catalysed by the nickel system, is achieved by controlling the rate of addition of the alkyl halide to the reaction mixture. When the aryl halide is present in excess, it reacts preferentially with the Ni(o) intermediate whereas the Ni(l) intermediate reacts more rapidly with an activated alkyl halide. Thus continuous slow addition of the alkyl halide to the electrochemical cell already charged with the aryl halide ensures that the alkyl-aryl coupled compound becomes the major product. Activated alkyl halides include benzyl chloride, a-chloroketones, a-chloroesters and amides, a-chloro-nitriles and vinyl chlorides [202, 203, 204], Asymmetric induction during the coupling step occurs with over 90 % distereomeric excess from reactions with amides such as 62, derived from enantiomerically pure (-)-ephedrine, even when 62 is a mixture of diastereoisomcrs prepared from a racemic a-chloroacid. Metiha-nolysis of the amide product affords the chiral ester 63 and chiral ephedrine is recoverable [205]. 

Reaction Chloro- benzene Benzyl chloride Cyclohexyl chloride... 

Synonym Gamma-Chloropropylene Oxide 3-Chloro-1,2-Propylene Oxide Chlorosulfonic Acid Chlorothene Chiorotoluene, Alpha Alpha-Chlorotoluene Omega-Chlorotoluene Chlorotrifluoroethylene Chlorotrimethylsilane Chlorsulfonic Acid Clilorylen Clip Chromic Acid Chromic Anhydride Chromic Oxide Chromium (VI) Dioxychloride Chromium Oxychloride Chromium Trioxide Chromyl Chloride Cianurina Citric Acid Citric Acid, Diammonium Salt Clarified Oil Clorox Cc Ral Coal Tar Oil Cobalt Acetate Cobalt Acetate Tetrahydrate Cobalt (II) Acetate Cobalt Chloride Cobalt (II) Chloride Cobaltous Acetate Cobaltous Chloride Cobaltous Chloride Dihydrate Cobaltous Chloride Hexahydrate Cobaltous Nitrate Cobaltous Nitrate Hexahydrate Cobaltous Sulfate Heptahydrate Cobalt Nitrate Cobalt (II) Nitrate Cobalt Sulfate Compound Name Epichlorohydrin Epichlorohydrin Chlorosulfonic Acid Trichloroethane Benzyl Chloride Benzyl Chloride Benzyl Chloride Trifluorochloroethylene Trimethylchlorosilane Chlorosulfonic Acid Trichloroethylene Cumene Hydroperoxide Chromic Anhydride Chromic Anhydride Chromic Anhydride Chromyl Chloride Chromyl Chloride Chromic Anhydride Chromyl Chloride Mercuric Cyanide Citric Acid Ammonium Citrate Oil Clarified Sodium Hypochlorite Coumaphos Oil Coal Tar Cobalt Acetate Cobalt Acetate Cobalt Acetate Cobalt Chloride Cobalt Chloride Cobalt Acetate Cobalt Chloride Cobalt Chloride Cobalt Chloride Cobalt Nitrate Cobalt Nitrate Cobalt Sulfate Cobalt Nitrate Cobalt Nitrate Cobalt Sulfate... 

Booth, S.C., Mould, A.J., Shaw, A. Gamer, R.C. (1983) The biological activity of 4-chloro-methylbiphenyl, benzyl chloride and 4-hydroxymethylbiphenyl in 4 short-term tests for carcinogenicity a report of an individual study in the UKEMS genotoxicity trial 1981. Mutat. Res., 119, 121-133... 

MacDonald, D. Telford, K. (1982) Drosophila, sex-linked recessive lethal tests with 4-chloro-methylbiphenyl and benzyl chloride. Mutat. Res., 100, 335-338... 

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