Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethylamine | HCID 8021 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 4,7-Dibromo-2,1,3-benzothiadiazole | HCID 626361 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 12090793 | HCID 12090793 | — |
Reaction Steps
4,7-Dibromobenzo[c][1,2,5]thiadiazole (1.02 g, 3.47×10−3 mol), Pd(PPh3)4 (0.207 g, 1.79×10−4 mol), CuI (0.029 g, 1.5×10−4 mol), THF (30 ml), diethylamine (3.0 ml) and (trimethylsilyl)acetylene (6.00 ml, 4.25×10−2 mol) were added to a 100-ml Schlenk tube. N2 was bubbled through the mixture for 5 min, following which the reaction was stirred at 45° C. for 20 h under N2. After cooling, the solvent was evaporated and the residue was chromatographed on silica gel with 1:1 hexanes:CHCl3 as the eluant. Yield=1.05 g (92% based on 1.02 g of 4,7-dibromobenzothiadiazole). 1H NMR (360 MHz, CDCl3): δ 7.70 (s, 2H, Ph-H), 0.33 (s, 18H, —Si—CH3). Chemical Ionization MS m/z: 328.0880 (M+) (calcd 328.089).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07842758B2 |
|---|
| Source dataset | uspto-grants-2010_11 |
|---|
| ORD ID | ord-06664e0ba9d24fa7aa044dd41bf0ef90 |
|---|
| Source note | uspto-grants-2010_11 |
|---|
