Potassium Carbonate → HCID 10292556, compound

HRID 585321Notes

Reaction equation

HRID 585321 reaction equation
[C:1]1(B(O)O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:37])[CH2:28][CH2:29][CH2:30][C:31](=[O:36])[C:32]([F:35])([F:34])[F:33])=[CH:23][CH:22]=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=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>[F:33][C:32]([F:34])([F:35])[C:31](=[O:36])[CH2:30][CH2:29][CH2:28][C:27]([C:24]1[CH:25]=[CH:26][C:21]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)=[CH:22][CH:23]=1)=[O:37]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 516892Sodium BicarbonateHCID 10268102HCID 10268102, compound

Product 1

HCID 10292556HCID 10292556, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

1.0 g 1-naphthaleneboronic acid, 1.0 g potassium carbonate and 0.06 g tetrakis(triphenylphosphine)palladium(0) in 90 ml toluene were combined under a protective gas atmosphere. A solution of 1.0 g 1-(4-bromophenyl)-6,6,6-trifluorohexane-1,5-dione in 10 ml toluene was added dropwise to this initial solution and it was stirred for 3 days at 90° C. It was allowed to cool to RT, 13 ml saturated aqueous sodium hydrogen carbonate solution was added dropwise thereto and the phases were separated. The organic phase was washed in succession with water, aqueous potassium hydrogen sulphate solution, water and saturated aqueous common salt solution. The organic phase was dried over sodium sulphate and the solvent was evaporated in the WV. Purification of the remaining residue by means of flash chromatography (stationary phase: silica gel, mobile phase: n-hexane/EA 3:2 v/v) and subsequent recrystallisation of the combined product fractions from EA/n-hexane (2:3) yielded 0.75 g of the title compound, m.p.=79.7-82.5° C.

Workup

  1. temperatureto cool to RT
  2. customthe phases were separated
  3. washThe organic phase was washed in succession with water, aqueous potassium hydrogen sulphate solution, water and saturated aqueous common salt solution
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. customthe solvent was evaporated in the WV
  6. customPurification of the remaining residue
  7. customby means of flash chromatography (stationary phase: silica gel, mobile phase: n-hexane/EA 3:2 v/v) and subsequent recrystallisation of the combined product fractions from EA/n-hexane (2:3)

Sources & evidence

ORD record
ord-e63a6eda15524e1e8daff3227a2a1fef
Source dataset
uspto-grants-2005_08
Patent number
US06930207B2

Reaction notes

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