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Sodium Carbonate → 7-(3,5-Dimethylphenyl)-2-methyl-1-indanone

HRID 2298472
Notes
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Reaction equation

HRID 2298472 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.[CH3:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[C:18]([CH3:20])[CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC1C=CC=CC=1C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:13][C:14]1[CH:15]=[C:16]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:10]=2[C:9](=[O:11])[CH:8]([CH3:12])[CH2:7]3)[CH:17]=[C:18]([CH3:20])[CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27343493,5-Dimethylphenylboronic acidHCID 117898227-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 221731007-(3,5-Dimethylphenyl)-2-methyl-1-indanoneYield 90.1%

Reagents, catalysts & solvents 3

HCID 167845
palladium(II) acetate
Catalyst
2×
HCID 962WaterSolvent2×
HCID 7237O-XyleneSolvent

Conditions

Temperature
100 °C

Procedure

Using a method similar to Example 16b), 16.25 g (0.09 mol) of (1), 14.85 g (0.1 mol) of 3,5-dimethylphenylboronic acid, 21.2 g (0.2 mol) of sodium carbonate were placed in 240 ml of o-xylene/80 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. After addition of 101 mg (0.45 mmol) of palladium acetate and 472 mg (1.8 mmol) of TPP, the reaction mixture was stirred for 8 hours at 100° C. After 2, 4 and 6 hours, the same amounts of palladium acetate and triphenylphosphine were added again each time. After addition of 150 ml of water, the phases were separated, the aqueous phase was extracted 3 times with 200 ml each time of ether, the combined organic phases were washed with 200 ml of water and 200 ml of saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent gave 20.3 g of (17) as an oil.

Workup

  1. customthe mixture was degassed a number of times
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted 3 times with 200 ml each time of ether
  4. washthe combined organic phases were washed with 200 ml of water and 200 ml of saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-e5abbbd49fa2470ea59afe5317c7a7b9
Source dataset
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06492539B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes