Sodium Carbonate → HCID 11497527, compound

HRID 458275Notes

Reaction equation

HRID 458275 reaction equation
FC(F)(F)S([C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:25]3[CH:30]=[CH:29][C:28](S(C(F)(F)F)(=O)=O)=[CH:27][CH:26]=3)[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:8][CH:7]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].[Cl:46][C:47]1[CH:52]=[CH:51][C:50](B(O)O)=[CH:49][CH:48]=1>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.O1CCCC1>[Cl:46][C:47]1[CH:52]=[CH:51][C:50]([C:6]2[CH:11]=[CH:10][C:9]([C:12]3([C:25]4[CH:30]=[CH:29][C:28]([C:50]5[CH:51]=[CH:52][C:47]([Cl:46])=[CH:48][CH:49]=5)=[CH:27][CH:26]=4)[C:24]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:18]4[C:13]3=[CH:14][CH:15]=[CH:16][CH:17]=4)=[CH:8][CH:7]=2)=[CH:49][CH:48]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 18442096HCID 18442096, compound

Product 1

HCID 11497527HCID 11497527, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

16 g of 9,9-bis[4-(trifluoromethylsulfonyl)phenyl]fluorene, 100 ml of tetrahydrofuran, 62 g of a 20% sodium carbonate aqueous solution, 8.54 g of 4-chlorophenylboronic acid, and 0.6 g of tetrakis(triphenylphosphine)palladium were placed in a 300 ml four-necked flask, and the mixture was heated at 70° C. The resulting mixture was aged at the same temperature for 18 hours, and the reaction mixture was then cooled to room temperature and subjected to liquid separation. An organic phase was washed with a saturated ammonium chloride aqueous solution and saturated salt water, and the resulting organic phase was concentrated and recrystallized from tetrahydrofuran to obtain 11.4 g of a white powder.

Workup

  1. temperaturethe reaction mixture was then cooled to room temperature
  2. customsubjected to liquid separation
  3. washAn organic phase was washed with a saturated ammonium chloride aqueous solution and saturated salt water
  4. concentrationthe resulting organic phase was concentrated
  5. customrecrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-7f7564d6205442bb8bac2011a1d2099f
Source dataset
uspto-grants-2007_03
Patent number
US07189877B2

Reaction notes

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