Dichloro methyl ether

Chloro-2 -trifluoroethyl dichloro-methyl ether Isoflurane... 

Synonyms BCME chloromethyl ether chloro(chloromethoxy)methane dichloro-methyl ether symmetrical dichloro-dimethyl ether dimethyl-1 -1dichloroether... 

Electrophilic Substitution Reactions of Monocyclic Thiophens. -The hazards connected with the use of chloromethyl and dichloro-methyl ether have attracted interest in alternative reagents for the chloromethylation of aromatics. A convenient reagent appears to be methoxyacetyl chloride and aluminium chloride in nitromethane... 

Aryl-l-chlorocyclopropanes s. 77,867 alkoxycyclopropanes from dichloro-methyl ethers s. Ang. Gh. 75, 670 (1963)... 

Fragmentation of alkoxyhalocarbenes (15) has been studied by product analysis, showing a prompt ability to capture HCl yielding mainly the corresponding dichloro-methyl ethers (16). In the presence of a base, the product profile was dramatically changed alkenes and chloroalkanes arising from CO extrusion were identified. The addition of a chloride source also favoured this fragmentation pathway. These results have been supported with LFP kinetic studies. 

Chemical Name 2,2-dichloro-1,1-difluoro-1-methoxyethane Common Name 1,1-difluoro-2,2-dichloroethyl methyl ether Structural Formula GHjOCF CHCI ... 

MalONIC ACID, ETHYLHYDROXY, DIETHYL ESTER, BENZOATE, 45, 37 Mfsitaidehydf, 47, 1 Mesitylcne, condensation with dichloro methyl methyl ether, 47, 1 Methalljl chloride in alkylation of 2,4-pentanedione with potassium carbonate, 47, 87... 

Notable examples of general synthetic procedures in Volume 47 include the synthesis of aromatic aldehydes (from dichloro-methyl methyl ether), aliphatic aldehydes (from alkyl halides and trimethylamine oxide and by oxidation of alcohols using dimethyl sulfoxide, dicyclohexylcarbodiimide, and pyridinum trifluoro-acetate the latter method is particularly useful since the conditions are so mild), carbethoxycycloalkanones (from sodium hydride, diethyl carbonate, and the cycloalkanone), m-dialkylbenzenes (from the />-isomer by isomerization with hydrogen fluoride and boron trifluoride), and the deamination of amines (by conversion to the nitrosoamide and thermolysis to the ester). Other general methods are represented by the synthesis of 1 J-difluoroolefins (from sodium chlorodifluoroacetate, triphenyl phosphine, and an aldehyde or ketone), the nitration of aromatic rings (with ni-tronium tetrafluoroborate), the reductive methylation of aromatic nitro compounds (with formaldehyde and hydrogen), the synthesis of dialkyl ketones (from carboxylic acids and iron powder), and the preparation of 1-substituted cyclopropanols (from the condensation of a 1,3-dichloro-2-propanol derivative and ethyl-... 

The reaction products from 2,4-dichlorophenol were tetrachloro-phenoxyphenols and tetrachlorodihydroxybiphenyls (Figure 5), as determined from their mass spectra and those of their methyl ethers. 4,6-Dichloro-2-(2, 4 -dichlorophenoxy)phenol (V) was the major phenoxy-phenol the mass spectral fragmentation pattern of o-hydroxyphenol ethers is quite characteristic since a hydrogen transfer occurs during the fragmentation (Figure 6). A trace of a trichlorophenoxyphenol also was detected and was formed presumably by the unsensitized reductive loss of chlorine, discussed previously. 

The use of a Lewis acid (e.g., friethylfluoroborate, zinc chloride, stannous chloride, titanium chloride, iron(m)chloride) and other reagents (e.g., iodine, trimethylsilane, trifluoiomethane-sulfonylsilane) have also been recommended. Exhaustive lists of catalysts and conditions can be found in reviews devoted to carbohydrates [5-7], or to general organic chemistry [27,28], However, one can add the new catalyst, which has been introduced for the smooth formation of p-methoxybenzylidene acetals and p-methaxy-phenylmethyl methyl ether [29], namely 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), and has been applied very recently [30] to the synthesis of isopropylidene mixed acetals. 

A solution of 22.1 g 2-methyl-4-(methylthio)anisole and 17.5 g dichloro-methyl methyl ether in 600 mL CH2C12 was vigorously stirred, and treated with 24.5 g anhydrous aluminum chloride added portion-wise over the course of 1 min. Stirring was continued for 20 min while the color developed to a dark red. There was added 500 mL H,0 with caution, and stirring was continued until the initial yellow solids redissolved and there were two distinct phases formed. These were separated, and the aqueous phase was extracted with 3x100 mL CH,C12. The... 

Dichloro-4-nitroaniline t-Butyl methyl ether Methanol Ethylenediamine... 

The third step was the conversation of l-(2-aminoethyl)-3-(2,6-dichloro-4-nitrophenyl)-thiourea ethylenediamine solvate to 2-[(2,6-dicloro-4-nitrophenyl)imino]imidazoline ethylenediamine solvate. (500 g, 1.35 mol) of above prepared thiourea solvate was suspended with toluene (4 L) and was heated at reflux for 15 hours. The mixture was cooled to 23°C and 1 M aqueous hydrochloric acid (4 L) was added. After stirring for 10 min the biphasic mixture was filtered to remove a sticky insoluble material. The aqueous phase was neutralized to pH=7.0 using 50% NaOH. After stirring for 1 hour the yellow solid was collected by filtration, washed with water (4 L) and t-butyl methyl ether (2 L) and dried in air to constant weight of 195 g (52%), m.p. 289-292°C. 

The fourth step was the conversation of 2-[2,6-dichloro-4-nitrophenyl) imino]imidazoline (150 g, 0.55 mol) in methanol (1,5 L) to 2-[(2,6-dichloro-4-aminophenyl)imino]imidazoline by hydrogen with 30 g Raney nickel catalyst at 23°C for 22 hours. After removing the catalyst hydrogen chloride gas was bubbled into solution until pH of the reaction mixture was 1.0. The solvent was rotary removed in vacuum and the residual solid was slurried with 2-propanol (1 L). The solvent was again removed by rotary evaporation, the cream solid was triturated with 2-propanol (600 ml). After aging for 1 hour, the solid was collected by filtration, washed with 2-propanol and t-butyl methyl ether, and dried for 15 hours at 6°C and t-butyl methyl ether, and dried for 15 hours at 60°C and 20 mm Hg. Yield of dihydrochloride 167 g... 

Chloro methyl diphenyl ether halfenprox Chloro methyl (dichloro) methyl silane flusilazole Chloro methyl ethyl ether acetochlor... 

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