HuagongsheHuagongshe Chemistry Print Report · For research reference only
Toluene → 2-(3-(Triphenylen-2-yl)phenyl)benzo[b]benzo[4,5]thieno[3,2-d]thiophene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 2-(3'-(Dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | HCID 68015595 | — |
| Reactant | 2-(3'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)benzo[b]benzo[4,5]thieno[3,2-d]thiophene Benzo[b]benzo[4,5]thieno[3,2-d]thiophen-2-yl trifluoromethanesulfonate | HCID 118130601 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Catalyst | 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl | HCID 11269872 | — |
| Solvent | Water | HCID 962 | — |
| Product | 2-(3-(Triphenylen-2-yl)phenyl)benzo[b]benzo[4,5]thieno[3,2-d]thiophene | HCID 86689409 | 78% |
Reaction Steps
Synthesis of 2-(3′-(dibenzo[b,d]thiophen-4-yl)-[1,1′-biphenyl]-3-yl)benzo[b]benzo[4,5]thieno[3,2-d]thiophene Benzo[b]benzo[4,5]thieno[3,2-d]thiophen-2-yl trifluoromethanesulfonate (1.3 g, 3.35 mmol), Pd2(dba)3 (0.061 g, 0.067 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.11 g, 0.268 mmol), 2-(3′-(dibenzo[b,d]thiophen-4-yl)-[1,1′-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.625 g, 3.51 mmol), K3PO4 (2.13 g, 10.04 mmol), toluene (90 mL) and water (10 mL) were charged in a 250 mL flask. This mixture was bubbled with nitrogen for 30 minutes then heated to reflux overnight. After purification, 1.5 g (78%) of a white solid was obtained. The compound was confirmed by NMR.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09447113B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-3dc8ec0aedd749c6b26b7ec33a7d586b |
| Source note | uspto-grants-2016_09 |