Water → HCID 22173443, compound

HRID 1062934Notes

Reaction equation

HRID 1062934 reaction equation
Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[CH:8]([CH3:12])[CH2:7]2.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(O)CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:12][CH:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:18]3[CH:19]=[CH:20][C:15]([C:14]([F:25])([F:24])[F:13])=[CH:16][CH:17]=3)[CH:3]=[CH:4][CH:5]=2)[C:9]1=[O:11]

Participants

7

Reactant 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 117898227-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 22173443HCID 22173443, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 174Ethylene GlycolSolvent

Conditions

Temperature
125 °C

Procedure

Using a method similar to Example 16 d), 6.28 g (0.035 mol) of (1), 7.6 g (0.040 mol) of 4-trifluoromethylphenylboronic acid and 8.16 g (77.3 mmol) of sodium carbonate were placed in 160 ml of ethylene glycol/17 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. After addition of 57 mg (0.283 mmol) of palladium acetate and 0.47 g (0.848 mmol) of TMSPP, the reaction mixture was stirred for 2 hours at 125° C. After addition of 170 ml of water, the aqueous phase was extracted 4 times with 100 ml each time of ether, the combined ether phases were washed with 60 ml of water and 60 ml of saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent gave 9.54 g of 2-methyl-7-(4-trifluoromethylphenyl)-1-indanone.

Workup

  1. customsimilar to Example 16 d
  2. customthe mixture was degassed a number of times
  3. extractionthe aqueous phase was extracted 4 times with 100 ml each time of ether
  4. washthe combined ether phases were washed with 60 ml of water and 60 ml of saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-a71a260203124f36924fa83f27b1ff7d
Source dataset
uspto-grants-2005_11
Patent number
US06963017B2

Reaction notes

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