[reaction: see text] A practical and efficient synthesis of aryl triflates under biphasic basic aqueous conditions is described. The current methodology provides entry into these valuable substrates that omits the use of amine bases and allows facile isolation by simple solvent evaporation after phase separation. Good yields can also be obtained without the use of organic solvent.

A series of isoindoline analogues with either an indazole (HMR 2934, HMR 2651) or benzisoxazole (HMR 2543) appendage were prepared for the proposed treatment of psychiatric disorders such as obsessive compulsive disorder and attention deficit disorder. The isoindoline compounds were prepared by reduction of the corresponding phthalimides with LiAlH 4 . One compound was not chiral, and the other two required an enantioselective synthesis. The key step for these optically active analogues involved the coupling by an S N 2 process of either a piperazynyl intermediate or a piperdinyl intermediate with methyl 3-benzyloxy-2-trifluoromethansulfonatopropionate. The products for these two analogues had >98% ee. Process improvements led to the multi-kilogram syntheses of each of these compounds.

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Sulfonic acids and estersSulfonic acids and esters Q 0550 Practical Synthesis of Aryl Triflates under Aqueous Conditions. -An efficient synthesis of aryl triflates from triflic anhydride and phenols either under biphasic basic aqueous conditions or under basic aqueous conditions is presented. Advantages of the present method are the avoidance of amine bases and the simple isolation by phase separation and evaporation. -(FRANTZ*, D. E.; WEAVER, D. G.; CAREY, J. P.; KRESS, M. H.; DOLLING, U. H.;

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