Water → 7-(3,5-Bis(trifluoromethyl)phenyl)-2-methyl-1-indanone

HRID 2298473Notes

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.[F:13][C:14]([F:29])([F:28])[C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(COC)OC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:13][C:14]([F:28])([F:29])[C:15]1[CH:16]=[C:17]([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:18]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Using a method similar to Example 15a), 6.75 g (0.03 mol) of (2), 8.5 g (0.033 mol) of 3,5-bis(trifluoromethyl)phenylboronic acid and 7.0 g (0.066 mol) of sodium carbonate were placed in 120 ml of dimethoxyethane and 36 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. 120 mg (0.5 mmol) of palladium acetate and 282 mg (1.1 mmol) of TPP were added and the reaction mixture was stirred for 2 hours at 80° C. After addition of 150 ml of water, the mixture was extracted 3 times with 150 ml each time of diethyl ether, the combined ether phases were washed 3 times with 150 ml each time of water and dried over magnesium sulfate. Removal of the solvent gave 9.93 g of (18) as an oil.

Workup

custom36 ml of water in the reaction vessel, the mixture was degassed a number of times
extractionthe mixture was extracted 3 times with 150 ml each time of diethyl ether
washthe combined ether phases were washed 3 times with 150 ml each time of water
dry with materialdried over magnesium sulfate
customRemoval of the solvent

Sources & evidence

ORD record: ord-c3ae24c7551d40888494890d48e9bcab
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492539B1

Reaction notes

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