Potassium Carbonate → HCID 21082911, compound

HRID 2236964Notes

Reaction equation

HRID 2236964 reaction equation
I[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]3([C:26]4[CH:25]=[C:24](I)[CH:23]=[CH:22][C:21]=4[C:20]4[C:15]3=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:4]=2[CH:3]=1.[C:28]1([N:34]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:35]2[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C([O-])([O-])=O.[K+].[K+].C(P([C:65]([CH3:68])([CH3:67])C)C(C)(C)C)(C)(C)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH:31]1[CH:32]=[CH:33][C:28]([N:34]([C:35]2[CH:40]=[CH:39][C:38]([C:2]3[CH:14]=[CH:13][C:12]4[C:11]5[C:6]([C:5]6([C:26]7[CH:25]=[C:24]([C:38]8[CH:39]=[CH:40][C:35]([N:34]([C:67]9[CH:65]=[CH:68][CH:49]=[CH:44][CH:45]=9)[C:28]9[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=9)=[CH:36][CH:37]=8)[CH:23]=[CH:22][C:21]=7[C:20]7[C:15]6=[CH:16][CH:17]=[CH:18][CH:19]=7)[C:4]=4[CH:3]=3)=[CH:7][CH:8]=[CH:9][CH:10]=5)=[CH:37][CH:36]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 121669344-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride)HCID 121855382,2'-Diiodo-9,9'-spirobi[fluorene]

Product 1

HCID 21082911HCID 21082911, compoundYield 597.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

2,2′-Diiodo-9,9′-spirobifluorene (2.84 g, 5.0 mmol), 4-(diphenylamino)phenylboronic acid (4.34 g, 15.0 mmol), Pd(PPh3)4 (0.289 g, 0.25 mmol), 2M K2CO3(aq) (25 ml) and tri-tert-butylphosphine (0.5 mmol) were mixed in a flask containing with toluene (50.0 mL). The mixture was refluxed 72 hours. The solution was extracted twice with chloroform. The combined organic extracts were dried (MgSO4) and concentrated by rotary evaporation. Column chromatography on silica gel (hexane/chloroform=3/1) afforded products as white solids 22DPASF (2.4 g, 60%).

Workup

  1. temperatureThe mixture was refluxed 72 hours
  2. extractionThe solution was extracted twice with chloroform
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-160f2a7204364b03a9aa8ec1b51d2cf0
Source dataset
uspto-grants-2010_05
Patent number
US07714145B2

Reaction notes

Loading…