Water → 2-Methyl-7-phenyl-1-indanone

HRID 2298465Notes

Reaction equation

Br[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.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(COC)OC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:12][CH:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:3]=[CH:4][CH:5]=2)[C:9]1=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

22.5 g (0.1 mol) of 7-bromo-2-methyl-1-indanone (2), 13.4 g (0.11 mol) of phenylboronic acid and 23.3 g (0.22 mol) of sodium carbonate were placed in 380 ml of dimethoxyethane and 120 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. 450 mg (2 mmol) of palladium acetate and 1.05 g (4 mmol) of triphenylphosphine (TPP) were added and the reaction mixture was stirred for 2 hours at 80° C. After addition of 300 ml of water, the mixture was extracted 3 times with 250 ml each time of diethyl ether, the ether phase was washed twice with 100 ml each time of water and dried over magnesium sulfate. Removal of the solvent gave 21.1 g of (15) as solid.

Workup

custom120 ml of water in the reaction vessel, the mixture was degassed a number of times
extractionthe mixture was extracted 3 times with 250 ml each time of diethyl ether
washthe ether phase was washed twice with 100 ml each time of water
dry with materialdried over magnesium sulfate
customRemoval of the solvent

Sources & evidence

ORD record: ord-cfbc8e703f8943d3ae02a5fba49f5e32
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492539B1

Reaction notes

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