Potassium Phosphate, Tribasic → HCID 87248987, compound

HRID 2068269Notes

Reaction equation

HRID 2068269 reaction equation
[C:1]([C:5]1[C:6](Br)=[CH:7][C:8]2[CH2:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([C:18]([CH3:21])([CH3:20])[CH3:19])=[C:12](Br)[CH:11]=3)([CH3:4])([CH3:3])[CH3:2].C1CCC(P([C:37]2[C:42]([C:43]3C=CC=CC=3)=[CH:41][CH:40]=[CH:39][CH:38]=2)C2CCCCC2)CC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:57]1([CH3:66])[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1B(O)O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1COCC1>[C:57]1([CH3:66])[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[C:6]1[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:17][C:16]2[C:15]3[C:10](=[CH:11][C:12]([C:41]4[CH:40]=[CH:39][CH:38]=[CH:37][C:42]=4[CH3:43])=[C:13]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:14]=3)[CH2:9][C:8]=2[CH:7]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27332672-Methylphenyl boronic acidHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 135475422,7-Dibromo-3,6-DI-tert-butyl-9H-fluorene

Product 1

HCID 87248987HCID 87248987, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen, 5.0 g (11.5 mmol) of 3,6-di-tert-butyl-2,7-dibromofluorene, 135 mg (0.60 mmol) of palladium(II) acetate, 603 mg (1.72 mmol) of (2-biphenyl)dicyclohexylphosphine, 14.5 g (68.3 mmol) of potassium phosphate, 4.7 g (34.6 mmol) of o-tolylboronic acid and 100 ml of THF were placed in a reaction container, and with stirring them at room temperature, 25 ml of water was slowly dropwise added. After the dropwise addition, the reaction solution was heated up to 50° C., and with stirring, the solution was heated for 10 hours. Thereafter, the reaction solution was quenched with 1N hydrochloric acid, and a soluble matter was extracted with ether. The organic phase was washed with water, a sodium hydrogencarbonate aqueous solution and a saturated saline solution. Thereafter, the thus washed organic phase was dried using magnesium sulfate, and the solvent was distilled off to obtain an unpurified desired product. The conversion ratio as measured by HPLC was 86%.

Workup

  1. additionAfter the dropwise addition
  2. temperaturethe reaction solution was heated up to 50° C.
  3. stirringwith stirring
  4. temperaturethe solution was heated for 10 hours
  5. customThereafter, the reaction solution was quenched with 1N hydrochloric acid
  6. extractiona soluble matter was extracted with ether
  7. washThe organic phase was washed with water
  8. customThereafter, the thus washed organic phase was dried
  9. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-0a504489620344eeaa4afb283b6abf38
Source dataset
uspto-grants-2012_10
Patent number
US08293856B2

Reaction notes

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