Reaction of phenylmagnesium bromide with halomethyl and α-bromobenzyl benzoates was written by Mizuch, K. G.;Gel’fer, Ts. M.. And the article was included in Doklady Akademii Nauk SSSR in 1950.Application In Synthesis of Chloromethyl benzoate This article mentions the following:
Addition of 4.25 g. ClCH6OBz to cold PhMgBr (from 2.9 g. Mg and 18.8 g. PhBr) in Et2O below 5°, followed by standing in an ice bath 1 hr. and refluxing 30 min. gave, after the usual treatment with NH4Cl solution, 1.5 g. Ph2, 2.5 g. (92%) PhCH2OH, b15 97-100°, and 5.95 g. (91.5%) Ph3COH; no BzOH was isolated. Similarly, BrCH2OBz gave 86% PhCH2OH and 87.5% Ph3COH, without any BzOH. PhMgBr (from 30.2 g. PhBr and 4.7 g. Mg) in Et2O with 11.64 g. PhCHBrOBz gave 60% Ph3COH, 1.6 g. Ph2, 3.2 g. Ph2CHOH (43.5%), 1.0 g. (10.4%) Ph3CH, 1.47 g. (11%) tetraphenolethane, m. 209.6-10.6° (from AcOH), and 0.61 g. (12.6%) BzOH. Similar reaction of PhMgBr (from 1.76 g. Mg and 12.3 g. PhBr) with 5.76 g. Ph2CHOBz gave 3.25 g. (88.2%) Ph2CHOH and 4.73 g. Ph3COH (90.9%), as well as 0.9 g. Ph2. The results are explained, at least in part, by the reaction of RMgX with the 1st C atom of the ROH involved in the ester structure, caused principally by the presence of sufficiently electrophilic groups in the vicinity of the ester link. In the experiment, the researchers used many compounds, for example, Chloromethyl benzoate (cas: 5335-05-7Application In Synthesis of Chloromethyl benzoate).
Chloromethyl benzoate (cas: 5335-05-7) belongs to organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. Alkyl chlorides readily react with amines to give substituted amines. Alkyl chlorides are substituted by softer halides such as the iodide in the Finkelstein reaction.Application In Synthesis of Chloromethyl benzoate
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics