Toluene → 2-(3-(Triphenylen-2-yl)phenyl)benzo[b]benzo[4,5]thieno[3,2-d]thiophene

HRID 64221Notes

Reaction equation

HRID 64221 reaction equation
C1C2C3[C:10]4[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=4SC=3SC=2C=CC=1OS(C(F)(F)F)(=O)=O.C1C2C3C=CC=CC=3SC=2C([C:38]2[CH:39]=[C:40]([C:44]3[CH:49]=[CH:48][CH:47]=[C:46]([C:50]4[CH:65]=[CH:64][C:53]5[S:54][C:55]6[S:59][C:58]7[CH:60]=[CH:61][CH:62]=[CH:63][C:57]=7[C:56]=6[C:52]=5[CH:51]=4)[CH:45]=3)[CH:41]=CC=2)=CC=1.[CH:66]1[C:74]2C3C=CC=CC=3SC=2C(C2C=C(C3C=CC=C(B4OC(C)(C)C(C)(C)O4)C=3)C=CC=2)=[CH:68][CH:67]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C:108]1(C)[CH:113]=CC=[CH:110][CH:109]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O>[CH:41]1[C:13]2[C:14]3[C:15](=[CH:113][CH:108]=[CH:109][CH:110]=3)[C:16]3[C:10](=[CH:74][CH:66]=[CH:67][CH:68]=3)[C:11]=2[CH:38]=[CH:39][C:40]=1[C:44]1[CH:45]=[C:46]([C:50]2[CH:65]=[CH:64][C:53]3[S:54][C:55]4[S:59][C:58]5[CH:60]=[CH:61][CH:62]=[CH:63][C:57]=5[C:56]=4[C:52]=3[CH:51]=2)[CH:47]=[CH:48][CH:49]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 680155952-(3'-(Dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 1181306012-(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

Product 1

HCID 866894092-(3-(Triphenylen-2-yl)phenyl)benzo[b]benzo[4,5]thieno[3,2-d]thiopheneYield 78%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 962WaterSolvent

Procedure

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.

Workup

  1. additionwere charged in a 250 mL flask
  2. customThis mixture was bubbled with nitrogen for 30 minutes
  3. temperaturethen heated
  4. temperatureto reflux overnight
  5. customAfter purification

Sources & evidence

ORD record
ord-3dc8ec0aedd749c6b26b7ec33a7d586b
Source dataset
uspto-grants-2016_09
Patent number
US09447113B2

Reaction notes

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