4- chloro-5-iodo

C7H6CII 1-chloro-2-iodo-4-methyl benzene 2401-22-1 522.15 46.016 1,2 10320 C7H6F3N 2-(trifluoromethyl)aniline 88-17-5 460.15 40.069 2... 

Hydroxy-de-amination 14 Halo(geno)-de-diazoniations 72, 75, 153, 194, 196, 221, 226, 402 f., see also Sandmeyer reaction, Astato-, Bromo-, Chloro-Iodo-de-dedazoniation Hydroxy-de-diazoniation... 

Nucleophilic substitution reactions have been less extensively investigated. The exchange reaction of 4-bromo-6,7-dimethyl-7,6-borazarothieno[3,2-c]pyridine with copper(I) salts in HMPT at 150-180 °C gives the chloro, iodo and cyano derivatives in good yields (e.g. equation 52). 

Substituted benzenes alkyl, fluoromethyl, chloro, iodo, hydroxy, nitro. 

This cyclization has also been observed in a variety of substituted azobenzenes,344 and is sometimes accompanied by the expulsion of methyl, chloro, iodo, and carbethoxy substituents from the position of cyclization. In the photocyclization of 2,4,6-trimethylazobenzene (328), a methyl migration is observed leading to the formation of... 

Furthermore, the concept of a sequential nucleophilic addition in acidic medium can be transposed to the conversion of the ynone intermediates with iodine monochloride [197] and subsequent cyclization [198] into chloro iodo furans in a one-pot fashion. Therefore, after coupling of (hetero)aroyl chlorides 7 and THP-protected propargyl alcohols 54, NaCl, iodine monochloride, and PTSA were added to give after 4 h of stirring at room temperature the substituted 3-chloro-4-iodo furans 59 in moderate to decent yields (Scheme 34) [196]. 

Chloro-4-iodo furans 59 can be valuable building blocks for the synthesis of highly substituted furans as illustrated by the Suzuki coupling of chloro iodo furan 59g with boronic acid 60d (R = p-MeOCeHU) furnishing trisubstituted chloro furan 62 in 59% yield (Scheme 36). Expectedly, the coupling selectively occurs at the carbon-iodine bond. 

Bis-[dimethyl-phenyl-phosphan]-carbonyl-chloro-iodo-per-fluoralkyl- XIII/9b, 337 frans-Bis-[triphenylphosphan]-carbonyl-polyhalogenphenyl-XIII/9b, 314... 

Both chlorines in the iminium chloride (27) can be replaced by fluorine, bromine or iodine, giving compounds (58)-(60) (Scheme 3) if the salt is treated with the corresponding hydrogen halide under anhydrous conditions. By chloro-iodo exchange with HI from the 3-chloroacrylamide chloride the corresponding amide iodide (61 equation 37) was prepared. Dimethylformamide chloride (27) is converted by methyl iodide to dimethylformamide iodide (59). Remarkably the difluoro compound (60) is a nonionic, distillable liquid which can be ionized by addition of boron trifluoride. ... 

The nitro, chloro, iodo, and proteo derivatives were found to be inactive in the MBS model. 

Kulstad and Malmsten (1980a) reported a remarkable synthesis of 1,10-diaza-18-crown-6 and cryptand[2.2.2] from the reaction of either l-iodo-8-chloro-3,6-dioxaoctane or l,8-diiodo-3,6-dioxaoctane. The chloro-iodo starting material gave the cryptand while the diiodo starting material gave the diaza-18-crown-6. In the former case, the iodide reacted much faster than the... 

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