The conversion of alcohols to halides using a filterable phosphine source

Chirally deuterated benzyl chlorides from benzyl alcohols via hexachloroacetone/polymer‐supported triphenylphosphine: synthesis of protected (2S, 3S)‐[3‐2H, 15N]‐tyrosine

“…Several halogenation conditions using alkoxyphosphonium intermediates to ensure inversion of the benzylic center during alcohol to halide conversion were investigated . Unfortunately, these reactions also produced by‐products, which interfered with or prohibited isolation of the labile halides, as others have also documented …”

Structural elucidation of a series of benzamide derivatives

“…The starting materials [ N ‐(6‐hydroxyhexyl)‐3,4‐dimethoxybenzamide ( 1 ), N ‐(6‐hydroxyhexyl)‐3,4,5‐trimethoxybenzamide ( 2 ), N ‐(8‐hydroxyoctyl)‐3,4‐dimethoxybenzamide ( 3 ), N ‐(8‐hydroxyoctyl)‐3,4,5‐trimethoxybenzamide ( 4 ), N ‐(10‐hydroxydecyl)‐3,4‐dimethoxybenzamide ( 5 ), N ‐(10‐hydroxydecyl)‐3,4,5‐trimethoxybenzamide ( 6 )] and their bromo derivatives N ‐(6‐bromohexyl)‐3,4‐dimethoxybenzamide ( 7 ), N ‐(6‐bromohexyl)‐3,4,5‐trimethoxybenzamide ( 8) , N ‐(8‐bromooctyl)‐3,4‐dimethoxybenzamide ( 9 ), N ‐(8‐bromoyoctyl)‐3,4,5‐trimethoxybenzamide ( 10 ), N ‐(10‐bromodecyl)‐3,4‐dimethoxybenzamide ( 11 ), N ‐(10‐bromodecyl)‐3,4,5‐trimethoxybenzamide were synthesized according to a procedure described in the literature …”

“…2.2 | Synthesis of benzamide derivatives (7)(8)(9)(10)(11)(12) The starting materials (5), N-(10-hydroxydecyl)-3,4,5trimethoxybenzamide (6)] and their bromo derivatives N-(6-bromohexyl)-3,4-dimethoxybenzamide (7), N-(6bromohexyl)-3,4,5-trimethoxybenzamide (8), 5-trimethoxybenzamide (10), N-(10bromodecyl)-3,4-dimethoxybenzamide (11), N-(10bromodecyl)-3,4,5-trimethoxybenzamide were synthesized according to a procedure described in the literature. [4,5] 2.3 | NMR spectroscopy 1 H and 13 C NMR data were acquired on a Bruker Avance III 400 NMR spectrometer operating at 400.15 and 100.62 MHz, respectively. For the 1 H NMR experiments, the relaxation delay was 90°pulse, spectral width of 8012 Hz and 65 K data points.…”

Design and Synthesis of Photoaffinity-Labeling Ligands of thel-Prolyl-l-leucylglycinamide Binding Site Involved in the Allosteric Modulation of the Dopamine Receptor

“…During the formation of the Boc-cis-4-bromoproline benzyl ester (6b), separation of the triphenylphosphine oxide from the product proved to be difficult. Therefore, this reaction was done with 1,2-bis(diphenylphosphino)ethane (diphos), 21 since approximately 70% of the diphos phosphine-oxide byproduct could be filtered off before column purification. Conversion of both 6a and 6b to their corresponding azides 7a and 7b was accomplished with inversion of configuration in each case.…”