Water → HCID 22173018, compound

HRID 2298485Notes

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.[C:13]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14].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:20]3[CH:21]=[CH:22][C:17]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:18][CH:19]=3)[CH:3]=[CH:4][CH:5]=2)[C:9]1=[O:11]

Participants

Conditions

Temperature: 125 °C

Procedure

Using a method similar to Example 16d), 2.0 g (0.011 mol) of (1), 2.31 g (0.013 mol) of 4-tert-butylphenylboronic acid and 2.6 g (24.6 mmol) of sodium carbonate were placed in 55 ml of ethylene glycol/5 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. After addition of 18 mg (0.09 mmol) of palladium acetate and 0.15 g (0.27 mmol) of TMSPP, the reaction mixture was stirred for 2 hours at 125° C. After addition of 60 ml of water, the aqueous phase was extracted 4 times with 60 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 2.8 g of 2-methyl-7-(4-tert-butylphenyl)-1-indanone.

Workup

customthe mixture was degassed a number of times
extractionthe aqueous phase was extracted 4 times with 60 ml each time of ether
washthe combined ether phases were washed with 60 ml of water and 60 ml of saturated sodium chloride solution
dry with materialdried over magnesium sulfate
customRemoval of the solvent

Sources & evidence

ORD record: ord-0eceda28853d4dadb1e83ecb1bf6538d
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492539B1

Reaction notes

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