P-fluorobenzyl chloride

Studies of alkyl halide-lithium alkyl reactions have been almost wholly concerned with proton polarization. The one exception to date is an investigation of polarization in the reaction of n-butyl lithium with p-fluorobenzyl chloride giving p,p -difluorobibenzyl (A/E multi-plet) and l-fluoro-4-pentylbenzene (E/A) (Rakshys, 1970). Surprisingly H-polarization is not observed. 

Net F-polarization (A at 56-4 MHz) has been observed during the reaction of p-fluorobenzyl chloride with sodium naphthalene in tetra-hydrofuran solution to give p, p -difluorobibenzyl (Rakshys, 1971). The spin selection is believed to take place within a radical pair of the -------------------------------F... 

Reaction of p-fluorobenzyl chloride with the anion of diethylmethylmalonate ester followed by saponification and decarboxylation leads to acid 9. Polyphosphoric acid cyclization leads to indanone 10. A Reformatsky reaction with zinc amalgam and bromo-acetic ester leads to carbinol 11 which is then... 

Ethyl 2-(p-fluorobenzyl)trifluoroacetoacetate reacted with resorcinol in 70 % sulfuric acid at 100 °C to provide coumarin 315a. Upon treatment with N,N-dimethylcarbamoyl chloride in the presence of NaH, this compound was readily converted into the corresponding iV,A -dimethylcarbamate 316a, which was tested as a TNF-a inhibitor [175]. A similar reaction of resorcinol with diethyl... 

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