DiChloromethyl chloroformate ether

Vilsmeier reaction), CICHOMe (from dichloromethyl methyl ether/titanium(iv) chloride), CC12 (from chloroform/sodium hydroxide, Reimer-Tiemann reaction), and 1,3-dithiane. 

Oxo-l//-2-henzotellurin (Isotellurocoumarin)3 2.9 g (10 mmol) of 2-(2 -chlorocarbonylphenyl)-ethenyl methyl tellurium and 100 mg of anhydrous zinc chloride are dissolved in 10 ml of dichloromethyl methyl ether and the mixture is kept overnight at 20°. The ether is evaporated and 50 ml of dry dichloromethane are added to the residue (the carboxylic acid chloride). This solution is cooled to — 80° and 1.33 g (10 mmol) of aluminum chloride are added with efficient stirring. The mixture is allowed to warm to 20°, it is then poured into 100 ml of ice/water. the mixture is extracted with chloroform, the extract is dried, and evaporated. The residue is recrystallized from hexane yield 0.77 g (30%) m.p. 83°. 

Carbon tetrachloride. Chloroform, 2-Chlorophenol, Cyclohexanol, Cyclopentene, 1,1-Dichloroethylene, irans-l, 2-Dichloroethylene, IV.yV-Dimethylaniline, lV,lV-Dimethylformamide, 2,4-Dimethylphenol, 2,4-Dinitrotoluene, 1,4-Dioxane, 1,2-Diphenylhydrazine, Ethyl formate. Formaldehyde, Glycine, Methanol, Methylene chloride. Methyl formate, 2-Methvlphenol. Monuron, 4-Nitrophenol, Oxalic acid, Parathion, Pentachlorophenol, Phenol, l idine. Styrene, Trichloroethylene, Vinyl chloride Formylacetic acid, see cis-l,3-Dichloropropylene, irans-1,3-Dichloropropylene IV-Formylcarbamate of 1-naphthol, see Carbaryl Formyl chloride, see Chloroethane, Chloroform, sym-Dichloromethyl ether, ds-1,3-Dichloropropylene, irans-ES-Dichloropropylene, Methyl chloride. Methylene chloride. Trichloroethylene, Vinyl chloride lV-Formyl-4-chloro-o-toluidine, see Chlornhenamidine. 

Hydracrylic acid, see p-Propiolactone Hydrazobenzene, see Aniline Hydriodic acid, see Methyl iodide Hydrobromic acid, see Bromodichloromethane, Bromoform, Methyl bromide, Metobromuron Hydrochloric acid, see Alachlor. Aldrin, Benzyl chloride, a-BHC, p-BHC, Bis (2-chloroethyl) ether, Bis(2-chloroisopropyl) ether, Bromacil. Bromodichloromethane, Carbon tetrachloride, Chloroethane, Chloroform, o-Chloronitrobenzene. Chloropicrin, Chloroprene, p-Chloronitrobenzene, 2,4-D, see Dalanon-sodium. p.p -DDD, p,p -DDT, Dicamba. 1,1-Dichloroethane, 1,1-Dichloroethylene, fratts-l,2-Dichloroethylene, s/m-Dichloromethyl ether, 2.3-Dichloronitrobenzene. 3.4-Dichloronitrobenzene. 1,2-Dichloropropane, cis-1,3-... 

Ethyl dichloroarsine. Dichloromethyl ether Trichloromethyl chloroformate Chloropicrin... 

Thus dichloromethyl methyl sulfone (2.02 g, 84 %) is formed when dichloromethyl methyl sulfide (1.93 g) and monoperphthalic acid (6.3 g) are kept in ether (200 ml) for several days. The sulfone, m.p. 71-72.5°, is isolated by removal of the ether, extraction with chloroform, and final recrystallization from chloroform-light petroleum or benzene-cyclohexane. 

In the presence of alkoxides chloroform reacts with secondary amines or azilidines to yield a mixture of aminal esters (486), amide acetals (487) and tris(dialkylamino)methanes (488 equation 224). Predominantly aminal esters (489 equation 225) are formed in the reaction of dichloromethyl ether with aziridines and sodium hydioxi. The heterocyclic aminal ester (491 equatimi 226) was prepared from the perimidine (490) and triethyl orthoformate. ... 

---