Water → HCID 22172929, compound

HRID 2298487Notes

Reaction equation

[CH2:1]([CH:5]1[CH2:13][C:12]2[C:7](=[C:8](Cl)[CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH2:2][CH2:3][CH3:4].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(O)CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([CH:5]1[CH2:13][C:12]2[C:7](=[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 125 °C

Procedure

Using a method similar to Example 16d), 10.02 g (0.045 mol) of 2-butyl-7-chloro-1-indanone, 6.58 g (0.054 mol) of phenylboronic acid and 11.9 g (0.122 mol) of sodium carbonate were placed in 135 ml of ethylene glycol/27 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. After addition of 5 mg (0.022 mmol) of palladium acetate and 0.051 g (0.09 mmol) of TMSPP, the reaction mixture was stirred for 5 hours at 125° C. After addition of 120 ml of water, the aqueous phase was extracted 4 times with 100 ml each time of ether, the combined ether phases were washed with 50 ml of water and 50 ml of saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent gave 12.0 g of (33) as an oil.

Workup

customthe mixture was degassed a number of times
extractionthe aqueous phase was extracted 4 times with 100 ml each time of ether
washthe combined ether phases were washed with 50 ml of water and 50 ml of saturated sodium chloride solution
dry with materialdried over magnesium sulfate
customRemoval of the solvent

Sources & evidence

ORD record: ord-fbc44c262f2e46358d80f5a5ee6841ac
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492539B1

Reaction notes

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