Potassium Phosphate, Tribasic → HCID 45279927, compound

HRID 1662127Notes

Reaction equation

HRID 1662127 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]([F:24])([F:23])[O:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([F:22])([F:21])([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[C:4]([F:25])[CH:3]=1.[CH2:26]([CH:31]1[CH2:36][CH2:35][CH:34]([C:37]2[CH:42]=[CH:41][C:40](B3OC(C)(C)C(C)(C)O3)=[CH:39][CH:38]=2)[CH2:33][CH2:32]1)[CH2:27][CH2:28][CH2:29][CH3:30].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1>[F:25][C:4]1[CH:3]=[C:2]([C:40]2[CH:39]=[CH:38][C:37]([CH:34]3[CH2:35][CH2:36][CH:31]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:32][CH2:33]3)=[CH:42][CH:41]=2)[CH:7]=[C:6]([F:8])[C:5]=1[C:9]([F:24])([F:23])[O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([F:22])([F:21])([F:20])([F:19])[F:18])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 46899408HCID 46899408, compoundHCID 58756055HCID 58756055, compound

Product 1

HCID 45279927HCID 45279927, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Into a vessel having an inner volume of 30 ml which was equipped with a stirring apparatus, a thermometer and a reflux condenser, 0.460 g (1.00 mmol) of 4-[(4-bromo-2,6-difluorophenyl)difluoromethoxy]pentafluorosulfanylbenzene, 0.411 g (1.15 mmol) of 4-(4-n-pentylcyclohexyl)-phenylboronic acid pinacol ester, 0.070 g (0.061 mmol) of tetrakis-(triphenylphosphine)palladium, 0.425 g (2.02 mmol) of tripotassium phosphate in the powder form and 5 ml of 1,4-dioxane were placed, and the reaction was allowed to proceed at 100° C. for 12 hours with stirring. After the reaction was completed, the reaction mixture was filtered, and the filtrate was concentrated under a reduced pressure. Then, the resulting residue was purified by the flush column chromatography (eluent: hexane), and 0.36 g (isolated yield: 59%) of 4-{[3,5-difluoro-4′-(4-n-pentylcyclohexyl)-biphenyl-4-yl]difluoromethoxy}pentafluorosulfanylbenzene was obtained as a white solid. The reaction scheme is shown in the following:

Workup

  1. customInto a vessel having
  2. customan inner volume of 30 ml which was equipped with a stirring apparatus
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under a reduced pressure
  5. customThen, the resulting residue was purified by the flush column chromatography (eluent: hexane)

Sources & evidence

ORD record
ord-b7c7e2aa8d6a423eb3dc1d0491f79fd4
Source dataset
uspto-grants-2011_10
Patent number
US08030512B2

Reaction notes

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