Complete recipeSource: SI
Route 1: Other
SI pp.3-4 · Synthesis of compound 1; Synthesis of compound 2; Synthesis of compound 3; Synthesis of compound 4; Synthesis of H8L · Figure S1
Metal precursorsnone
Linker precursors2,6-dihydroxytoluene; paraldehyde; CH2ClBr; dimethyl 5-hydroxyisophthalate; compound intermediates 1-4
Solventswater, ethanol, DMF, CCl4, dichloromethane, acetonitrile, CH2Cl2/EtOH, THF/H2O
Additives37% HCl, K2CO3, N-bromosuccinimide, AIBN, nitric acid
AtmosphereN2 protection for compound 2, compound 4, and H8L steps; not stated for compound 1 and 3 except reflux.
Temperature80; 80; reflux in CCl4; 80; 75
Time16; 8; 8; 27; 12
Oxidant / reductantN-bromosuccinimide/AIBN bromination in compound 3 step; nitric acid used for acidification to pH about 1 in final H8L step.
Work-upWashing with cold ethanol-water, extraction with saturated NaCl, drying over Na2SO4, silica gel chromatography, recrystallisation from CH2Cl2/EtOH, water wash, THF evaporation, acidification and water evaporation.
Activationnot applicable
Scalability contextMultigram ligand precursor synthesis reported with yields for intermediates and final H8L.
Show 12 structured reagent records
| Role | Reagent | Amount / concentration | Source |
|---|---|---|---|
| Linker | 2,6-dihydroxytoluene | 10.28 g, 80 mmol | SI pp.3-4 · Synthesis of compound 1; Synthesis of compound 2; Synthesis of compound 3; Synthesis of compound 4; Synthesis of H8L · Figure S1 |
| Other | paraldehyde | 3.53 g, 80 mmol | SI pp.3-4 · Synthesis of compound 1; Synthesis of compound 2; Synthesis of compound 3; Synthesis of compound 4; Synthesis of H8L · Figure S1 |
| Acid | 37% aqueous HCl | 50 mL · 37% | SI pp.3-4 · Synthesis of compound 1; Synthesis of compound 2; Synthesis of compound 3; Synthesis of compound 4; Synthesis of H8L · Figure S1 |
| Solvent | water | 100 mL | SI pp.3-4 · Synthesis of compound 1; Synthesis of compound 2; Synthesis of compound 3; Synthesis of compound 4; Synthesis of H8L · Figure S1 |
| Solvent | ethanol | 100 mL | SI pp.3-4 · Synthesis of compound 1; Synthesis of compound 2; Synthesis of compound 3; Synthesis of compound 4; Synthesis of H8L · Figure S1 |
| Base | anhydrous K2CO3 | 25.06 g, 181.5 mmol; 2.5 g, 18 mmol; 5.56 g, 40 mmol | SI pp.3-4 · Synthesis of compound 1; Synthesis of compound 2; Synthesis of compound 3; Synthesis of compound 4; Synthesis of H8L · Figure S1 |
| Additive | CH2ClBr | 20 mL | SI pp.3-4 · Synthesis of compound 1; Synthesis of compound 2; Synthesis of compound 3; Synthesis of compound 4; Synthesis of H8L · Figure S1 |
| Oxidant | N-bromosuccinimide (NBS) | 11.84 g, 66.3 mmol | SI pp.3-4 · Synthesis of compound 1; Synthesis of compound 2; Synthesis of compound 3; Synthesis of compound 4; Synthesis of H8L · Figure S1 |
| Additive | azodiisobutyronitrile (AIBN) | catalytic amount | SI pp.3-4 · Synthesis of compound 1; Synthesis of compound 2; Synthesis of compound 3; Synthesis of compound 4; Synthesis of H8L · Figure S1 |
| Linker | dimethyl 5-hydroxyisophthalate | 3.78 g, 18 mmol | SI pp.3-4 · Synthesis of compound 1; Synthesis of compound 2; Synthesis of compound 3; Synthesis of compound 4; Synthesis of H8L · Figure S1 |
| Solvent | tetrahydrofuran (THF) | 400 mL | SI pp.3-4 · Synthesis of compound 1; Synthesis of compound 2; Synthesis of compound 3; Synthesis of compound 4; Synthesis of H8L · Figure S1 |
| Acid | nitric acid | acidified until pH about 1 | SI pp.3-4 · Synthesis of compound 1; Synthesis of compound 2; Synthesis of compound 3; Synthesis of compound 4; Synthesis of H8L · Figure S1 |