Potassium Phosphate, Tribasic → HCID 86689411, compound

HRID 871123Notes

Reaction equation

HRID 871123 reaction equation
FC(F)(F)S(O[C:7]1[CH:22]=[CH:21][C:10]2[S:11][C:12]3[S:16][C:15]4[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=4[C:13]=3[C:9]=2[CH:8]=1)(=O)=O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[CH:54]1[C:62]2[C:61]3[CH:63]=[CH:64][CH:65]=[CH:66][C:60]=3[S:59][C:58]=2[C:57]([C:67]2[CH:68]=[C:69]([C:73]3[CH:78]=[CH:77][CH:76]=[C:75](B4OC(C)(C)C(C)(C)O4)[CH:74]=3)[CH:70]=[CH:71][CH:72]=2)=[CH:56][CH:55]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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].O.C1(C)C=CC=CC=1>[CH:54]1[C:62]2[C:61]3[CH:63]=[CH:64][CH:65]=[CH:66][C:60]=3[S:59][C:58]=2[C:57]([C:67]2[CH:68]=[C:69]([C:73]3[CH:78]=[CH:77][CH:76]=[C:75]([C:7]4[CH:22]=[CH:21][C:10]5[S:11][C:12]6[S:16][C:15]7[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=7[C:13]=6[C:9]=5[CH:8]=4)[CH:74]=3)[CH:70]=[CH:71][CH:72]=2)=[CH:56][CH:55]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 680155952-(3'-(Dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86689410HCID 86689410, compound

Product 1

HCID 86689411HCID 86689411, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

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. customThis mixture was bubbled with nitrogen for 30 minutes
  2. temperaturethen heated
  3. temperatureto reflux overnight
  4. customAfter purification

Sources & evidence

ORD record
ord-2b2ed60b055d4f83a81d1c633dd16171
Source dataset
uspto-grants-2015_03
Patent number
US08969592B2

Reaction notes

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